DELIVERABLE 04 · ROADMAP & MILESTONES Project Roadmap & Milestones Phase-by-phase delivery plan from Phase 1 kickoff through production go-live — 13 months, 5 phases, 40+ milestones. PREPARED FOR SPONSOR BY VERSION Resortments Russ · Owner Webaroo v3.0 Project Roadmap & Milestones This roadmap is prepared to translate the Project Charter into a sequenced, time-boxed delivery plan — phase-by-phase, milestone-by-milestone, from Phase 1 kickoff through production go-live in 14 months. Our delivery cadence rests on four core imperatives: 1. Compress time-to-working-software. Phase 1 delivers in ~120 days — Foundation platform plus Land Division pilot — so Russ sees real parcels, real cost data, and a real workflow handoff by Month 4. 2. Sequence by operational ROI, not by organizational politics. Wave 1 (Phase 2) tackles Legal Close Land, Material Procurement, and Plant Division — the three divisions with the highest documented pain points. Wave 2 (Phase 3) handles Field, Management/Leasing, and Legal Rollovers. 3. Build the foundational platform once; deliver division-specific modules iteratively across phases. Auth, workflow engine, DMS, and the Accounting Hub schema ship in Phase 1. Every subsequent module extends that foundation — no re-architecting. 4. Mobile and advanced features follow a working web baseline. iOS/Android apps ship in Phase 4 against a stable, battle-tested web platform — not simultaneously with it. Project Vision: Build a comprehensive unified web and mobile platform serving 8 divisions of Resortments, replacing fragmented systems with integrated workflows, real-time visibility, and intelligent automation. Scope: 8 divisions, 40+ users, 5 access tiers, enterprise-grade security, mobile-first field operations. Phase 0: Discovery & Scoping Timeline: March – April 2026 Status: In Progress Sponsor: Russ (Resortments Owner) Delivery: Webaroo (full platform design, development, and delivery) Objectives Complete stakeholder engagement, validate architecture, and secure formal scope sign-off. Activities & Deliverables ACTIVITY STATUS NOTES Stakeholder ✅ Land, Legal Close Land, Material Procurement, ADP/Payroll, Field, Complete Management/Leasing, Plant, Accounting Hub divisions complete ✅ Completed April 8, 2026; confirmed multi-entity QB, ADP payroll for 12 Complete employees, cost allocation engine, 13–17 dev-months HIGH complexity ✅ Documented data silos, legacy systems, integration gaps ✅ Microservices API, PostgreSQL, React/React Native, cloud infrastructure ⏳ In Division modules, data flows, integration requirements ⏳ Pending Obtain approval on scope, timeline, resource commitment interviews (8/8) Accounting Hub interview Current state audit Complete Architecture decision Formal scope documents Stakeholder signoff Complete Progress Key Decisions Made Tech Stack: Node.js/Express backend, PostgreSQL, React (web), React Native (mobile), AWS/GCP cloud deployment Database Approach: Unified schema with division-specific views; centralized Accounting Hub data model Integration Priority: QuickBooks (financial), RealPage/OneSite (leasing), DocuSign (closings), ADP (payroll) Auth Strategy: OAuth 2.0 + custom role-based access control (5 tiers) Key Risks / Blockers Accounting Hub: Interview complete; scope confirmed and documented RealPage API: Unconfirmed access and data availability (critical for Leasing module) Data Quality: Scattered sources (email, OneDrive, sheets, phone notes); digitization needed Milestone: Discovery Complete ✓ Gate Criteria: - All 8 stakeholder interviews complete - Formal scope document approved by leadership Architecture & tech stack validated - Resource plan and budget baseline established - Phase 1 kickoff scheduled Phase 1: Foundation / MVP Timeline: May – August 2026 (4 months) Payment: $300,000 collected upfront at SOW signing — see Payment Schedule & Terms document Owner: Webaroo Engineering Lead, Product Manager Key Outcome: Russ can log in, see Land Division parcels with real cost data, and verify one cross-division workflow handoff (Land → Legal Close) routing correctly Core Components 1.1 AUTHENTICATION & AUTHORIZATION SYSTEM SSO Integration (OAuth 2.0, SAML support) 5-Tier Role-Based Access Control: Owner (Russ) — owner dashboard, all data, all actions Executive (Russ as Owner/Executive; Johnny CPA as Accounting Lead) — view financial & operational dashboards Manager (Division leads) — full access to division + cross-division reads User (Operations staff) — division-specific read/write Viewer (Consultants, vendors) — read-only curated views Two-Factor Authentication (2FA) — SMS + authenticator app options Session Management — token expiry, device tracking, login audit logs 1.2 CORE DATABASE SCHEMA DESIGN Unified Data Model: Companies → Divisions → Projects → Transactions Entities: Users, Roles, Permissions, Divisions, Projects, Documents, Audit Logs Accounting Hub Schema: GL Accounts, Cost Centers, Payment Methods, Transaction Ledger Division Base Tables: Asset/Property, Personnel, Contracts, Work Orders Integration Tables: QB sync state, RealPage cache, DocuSign envelope tracking Data Retention: 7-10 year archive tables for compliance 1.3 API LAYER ARCHITECTURE RESTful API (with GraphQL query layer for advanced uses) Endpoints: Auth, Users, Divisions, Projects, Documents, Accounting, Integrations Rate Limiting & Throttling — per-user quotas Webhook Handlers — inbound from RealPage, DocuSign, ADP API Documentation — auto-generated (Swagger/OpenAPI) 1.4 OWNER DASHBOARD (UNIFIED COMPANY / EXECUTIVE VIEW) Real-Time KPIs: Active projects by division Financial snapshot (revenue, costs, margin by division) Document volume (pending, completed, overdue) User activity feed System health & integration status Division Drill-Down: Click to see full division analytics Search & Filter: Global search across all divisions and documents Customizable Widgets: Russ can configure what appears on home page 1.5 ACCOUNTING HUB MODULE Central Financial Data Repository GL Account master, Cost Center structure Chart of Accounts (aligned to QB) Payment methods, bank accounts, credit cards QuickBooks Integration: Read GL accounts, cost centers Sync transactions (optional pull-only initially) Payment recording & reconciliation Monthly close reporting Cash Flow Forecast — 12-month rolling projection by division Budget Tracking — vs. actuals, variance analysis Audit Trail — all financial transactions logged with user/timestamp 1.6 BASIC WORKFLOW ENGINE Division-to-Division Handoffs: Land → Legal Close Land (handoff to David) Land → Material Procurement (draw orders trigger PO requests from Tracy) Field → Management/Leasing (completion triggers leaseback processing) Workflow States: Draft → Submitted → Approved → In Progress → Complete Automated Triggers: Email notifications, dashboard alerts, escalation rules Audit Trail: Who did what, when, and with what data 1.7 DOCUMENT MANAGEMENT SYSTEM (DMS) Central Repository: Upload, version control, full-text search Multi-format support (PDF, images, spreadsheets, videos) Access control per document Integration Points: DocuSign envelope lifecycle tracking QuickBooks receipt attachment RealPage document linking Retention Policies: Auto-archive after 7+ years Comment & Annotation: Mark up documents in-app Phase 1 Deliverables Auth system deployed (SSO, 2FA, 5-tier RBAC) PostgreSQL schema v1.0 in production REST API fully documented, rate-limited Owner Dashboard fully functional Accounting Hub module live (QB read-only) Basic workflow engine deployed (Land → Legal, → Material) DMS with 10GB storage per user All systems monitored, alerting in place Phase 1 Testing & Validation Timeline: August 1 – August 31, 2026 (final month of Phase 1; must complete before MVP Launch milestone) UAT: Russ (Owner/Executive), Johnny CPA (Accounting Lead), Finance team validate Accounting Hub Load Testing: 40 concurrent users, 100K documents indexed Security Audit: Penetration testing, RBAC validation Integration Testing: Mock QB, RealPage, DocuSign flows Milestone: MVP Launch ✓ Gate Criteria: - Russ logs in, sees unified data across all divisions - Auth system enterprise-ready (SSO, 2FA working) - Accounting Hub showing GL & cost data - Workflow engine routing tasks correctly - DMS storing and retrieving documents reliably - API stable under load (99.5% uptime) - All 40 users onboarded with access - Zero security findings from audit Phase 2: Division Modules — Wave 1 Timeline: September – December 2026 (4 months) Payment: $700,000 released on Phase 2 completion and UAT sign-off Owner: Webaroo Product & Engineering Teams Parallel Workstreams: Land & Legal Close Land; Material Procurement; Integrations (coordinated timing) Why Wave 1: High-Priority, High-Impact Divisions Land Division (Russ's core): Drives revenue, highest pain points documented Legal Close Land (David): Directly connected to Land handoffs, David owns 2 divisions Material Procurement (Tracy): 2000+ POs annually; largest data volume challenge Integrations: ADP, DocuSign (foundational for all divisions) 2.1 Land Division Module Owner: Russ Key Processes: Site acquisition, financing, cost tracking, deliverables, closeout DATA MODEL Assets: Property ID, address, acreage, legal description, acquisition date, cost Financing: Loan details, draw schedule, interest rates, lender, payment schedule Costs: Hard costs (land, construction), soft costs (legal, permits), contingency Status Tracking: Open, Under Development, Complete, Closed WORKFLOWS Acquisition to Closeout: Site identified → Financing approved → Land purchased → Permits obtained → Closeout approved → Legal Close initiated Cost Tracking: Real-time cost rollup by category (hard, soft, contingency) Draw Management: Financing draws linked to milestones, payment recording FEATURES Property Dashboard: Active sites, cost status, financing timeline Cost Tracker: Budget vs. actual, cost overruns, approval workflows Document Linking: Contracts, surveys, permits, appraisals Financial Integration: Costs flow to Accounting Hub GL INTEGRATION → Legal Close Land: Triggers legal closing workflow for David → Material Procurement: Construction cost estimates trigger PO authorizations SUCCESS METRICS Russ can see all active properties with real-time cost status 100% of financing draws recorded in system Cost overruns flagged automatically within 24 hours Handoff to Legal Close Land fully automated 2.2 Legal Close Land Module Owner: David Key Processes: Title work, closing mechanics, entity formation, post-closing filings DATA MODEL Closing Package: Land property reference, parties, timeline, closing date Title Search: Abstract, title report, title insurance Deed & Documents: Prepared, signed, recorded Entity Formation: Corporate entity type, EIN, registered agent Post-Closing: Recording confirmation, CD&A (Commitment, Deed, & Affidavit), notice filing WORKFLOWS Closing Initiation: Land Division signals site ready → Legal Close workflow starts Document Preparation: Title review → Deed drafted → Closing statement prepared Signing & Recording: Documents signed → Recorded with county → Confirmation Post-Close: Entity setup → IRS filing → Lender notification FEATURES Checklist View: Closing document status (pending, signed, recorded, filed) Timeline Tracker: Key dates (abstract received, closing, recording, filing) Integration with DocuSign: Documents sent for signature, tracking envelope status Title Company Link: Request abstract, title insurance, coordinate closing INTEGRATION ← Land Division: Receives handoff from Russ's team → Management/Leasing: After closing complete, property ready for leaseback SUCCESS METRICS All closings tracked from initiation to post-close DocuSign envelopes created and tracked automatically Zero missed recording deadlines Post-close entity setup completed on schedule 2.3 Material Procurement Module Owner: Tracy Key Processes: Request → Quote → PO → Receipt → Invoice → Payment DATA MODEL Purchase Requests: Requester, project, item description, quantity, budget Vendors: Vendor DB, pricing history, contract terms, payment terms Purchase Orders: PO#, vendor, items, quantities, unit prices, delivery date, cost Receiving: Receipt log, delivered items, quantity verification, quality inspection Invoices: Vendor invoice, PO match, line-item reconciliation Payments: Check/ACH, vendor account, reconciliation to GL WORKFLOWS Request Creation: Land division needs materials → Tracy receives request → Approves → Creates PO Vendor Quote: 3-quote process for items >$5K PO Issuance: Auto-numbered, sent to vendor via email/portal Delivery Tracking: Scheduled delivery, actual receipt, QA inspection Invoice Matching: 3-way match (PO ↔ Invoice ↔ Receipt), dispute resolution Payment: Auto-payment on net terms, accrual to GL FEATURES Vendor Master: Searchable database, pricing tables, contact info, payment terms PO Dashboard: Open POs, aging analysis, overdue deliveries, cost trends Receiving Station: Mobile-friendly receipt entry, photo documentation Invoice Portal: Drag-and-drop invoice upload, 3-way match validation Cost Analysis: Spend by vendor, by category, price trends, savings tracking Budget Integration: Real-time commitment to GL cost centers HIGH-VOLUME HANDLING 2000+ annual POs: Batch import, bulk operations, bulk email distribution 100,000+ line items: Fast search, filtering, export to Excel Multi-location delivery: Vendor dropdown, autocomplete address lookup Duplicate detection: System flags duplicate POs INTEGRATION ← Land Division: Budget allocations, draw authorizations, line items → Accounting Hub: Costs flow to GL, accruals to balance sheet Vendor Integration: Email notifications, supplier portal (Phase 4) SUCCESS METRICS All 2000+ annual POs created in system (no email-only POs) 3-way match pass rate >95% Delivery receipt within 2 days of arrival Invoice-to-payment cycle <30 days Real-time budget visibility across all projects 2.4 ADP Integration Owner: Webaroo Integration Engineer Key Data: Employee roster, payroll runs, taxes, benefits, time tracking SCOPE Inbound (ADP → Resortments): Employee master (ID, name, email, department, cost center, manager) Payroll summary (gross, net, taxes, deductions) Time tracking (if available) Benefits enrollment, changes Outbound (Resortments → ADP): New hire setup (optional, MVP: manual) Termination notifications (optional) Sync Cadence: Daily for payroll, weekly for roster FEATURES Employee Directory: Auto-synced from ADP, searchable by division/manager Payroll Dashboard: Monthly payroll summary, cost distribution to GL Allocation Tracking: Employee costs assigned to projects, cost centers Manager View: Reports of their direct reports, payroll details SUCCESS METRICS Daily sync of ADP data with <5% failure rate 100% of payroll costs allocated to correct GL codes Employee directory always current (within 24 hours of ADP change) 2.5 DocuSign Integration Owner: Webaroo Integration Engineer Key Requirement: ~500 document types × ~20 closings = ~10,000 active envelopes annually SCOPE Inbound (DocuSign → Resortments): Envelope creation, template linking Recipient tracking (sent, viewed, signed, declined) Signature capture, audit trail Completion/voiding events Outbound (Resortments → DocuSign): Envelope initiation (Legal Close module triggers deed signing) Template selection (deed, closing statement, affidavits) Recipient assignment (grantor, grantee, notary, witnesses) Scale: Queue management, rate limiting, bulk operations FEATURES Envelope Tracker: View status of all envelopes, drill down to signers Template Management: Curated list of approved templates (deed, power of attorney, disclosure, etc.) Integration with Legal Close Module: Automatic envelope creation on workflow trigger Bulk Sending: Multi-envelope initiation for volume closings Compliance: Audit logs, signed copy storage in DMS PERFORMANCE REQUIREMENTS 10,000 envelopes/year = ~27/day peak API rate limits: Batch operations, exponential backoff Retry logic: Webhook delivery failures, queue recovery Timeout handling: Long-running signing sessions SUCCESS METRICS Zero envelope delivery failures (99.9% uptime) Envelope status updates within 5 minutes of event Scale test: 500 envelopes/day without degradation <2% webhook delivery failures Phase 2 Dependencies & Sequencing Inputs from Phase 1 (must be stable before Phase 2 kickoff): Authentication, Database schema, API layer, Workflow engine, Document Management System, Accounting Hub schema, Land Division pilot. Phase 2 modules and owners: MODULE DIVISION DEPENDS ON FEEDS INTO David Phase 1 Land pilot (handoff trigger), Accounting Hub (closing McDaniel DocuSign integration financials) Tracy Phase 1 Land pilot (cost flow), Phase 3 Plant Division (vendor + Accounting Hub (GL sync) inventory data) OWNER Legal Close Land Material Procurement ADP Integration Webaroo Eng Accounting Hub All division payroll roll-ups DocuSign Webaroo Eng Auth + DMS Legal Close Land (envelope Integration creation) Outputs to Phase 3: All Phase 2 modules must reach UAT sign-off before Phase 3 kickoff. Field, Management/Leasing, Legal Rollovers, and Plant modules all consume data and workflows established in Phase 2. Phase 2 Deliverables Land Division module fully operational Legal Close Land module fully operational Material Procurement module handling all 2000+ POs ADP integration syncing daily with <5% error rate DocuSign integration scale-tested to 500 envelopes/day All workflows between divisions automated Russ + David + Tracy can operate fully in system Finance can track all costs to GL Milestone: Core Operational Divisions Live ✓ Gate Criteria: - Land module in production, no manual workarounds - Legal Close Land fully automated via DocuSign - Material Procurement: 100% of POs in system - ADP roster always current (within 24 hours) All 3-way matches passing automatically - Financial data flowing cleanly to Accounting Hub - Russ can see real-time cost status across all 3 divisions - Zero critical defects in production Phase 3: Division Modules — Wave 2 Timeline: January – March 2027 (3 months) Payment: $700,000 released on Phase 3 completion and UAT sign-off Owner: Webaroo Product & Engineering Teams Dependencies: Phase 2 complete, Wave 1 divisions stable Why Wave 2: Supporting Divisions + Special Cases Plant Division (Zac): New physical facility coming online; high complexity, lower urgency Field Division (Gerardo): Crew tracking, geo-fencing, asset management; mobile-critical Management/Leasing (Dylan): Largest portfolio; RealPage integration core dependency Legal Rollovers (David): Lightweight, complements his Land closings; David availability 3.1 Plant Division Module Owner: Zac Key Processes: Equipment procurement, maintenance scheduling, production planning, asset tracking CONTEXT & ASSUMPTIONS Plant not yet operational (coming online during Phase 3) Design must accommodate: Future expansion, equipment additions, downtime scheduling Key Integration: ADP (staff assigned to plant), Material Procurement (spare parts), Accounting (OpEx tracking) DATA MODEL Assets: Equipment ID, description, manufacturer, model, acquisition cost, depreciation schedule Maintenance: Scheduled vs. unscheduled, technician assignment, downtime duration Production: Scheduled production runs, actual output, efficiency metrics, scrap tracking Inventory: Spare parts inventory, reorder levels, vendor links Staffing: Crew assigned to plant shifts, cross-trained roles, capacity planning WORKFLOWS Equipment Procurement: Zac requests equipment → Material Procurement sourcing → Asset added to system Maintenance Scheduling: Preventive vs. reactive, technician dispatch, downtime notification Production Planning: Weekly production schedule → Crew assignment → Execution → Actual report Asset Lifecycle: Acquisition → Commissioning → Maintenance → Depreciation → Disposal FEATURES Asset Dashboard: Real-time equipment status, maintenance status, downtime tracking Maintenance Schedule: Preventive schedule, actual maintenance history, technician notes Production Dashboard: Daily production, actual vs. plan, efficiency metrics Spare Parts Inventory: Current levels, reorder triggers, vendor contacts Integration with Material Procurement: Equipment and spare parts sourced through Tracy SUCCESS METRICS All plant assets tracked in system with depreciation schedules Maintenance schedule created and adhered to Production data capturing daily (or per-shift) Equipment downtime <5% unplanned (95%+ uptime on critical assets) 3.2 Field Division Module Owner: Gerardo Key Processes: Crew assignment, work orders, site inspections, geo-tracking, equipment allocation DATA MODEL Crews: Crew ID, crew members, equipment assigned, certifications, home base Work Orders: Site location, scope, crew assignment, schedule, status, completion signature Inspections: Inspection type (safety, quality, compliance), inspector, date, findings, photo evidence Assets: Field equipment (tools, vehicles, trailers), location tracking, maintenance Time & Attendance: Daily time logs, site check-in/out, travel time, overtime Compliance: OSHA safety incidents, near-miss reports, corrective actions WORKFLOWS Work Order Creation: Site needs work → Gerardo or manager creates WO → Assigns crew with skills Crew Dispatch: Route optimization, travel time calculation, asset assignment On-Site Execution: Check-in with geo-stamp, time logging, photo documentation, inspection Completion & Sign-Off: Site rep/customer signs completion, crew signs off, data synced Compliance Tracking: Incident reports, corrective action tracking, audit trail FEATURES Mobile App (iOS/Android): Work order list with directions to site Real-time crew location (geo-fencing, asset tracking) Time clock (check-in/out, task break-down) Photo/video capture, annotation Signature capture (site completion) Offline mode with sync on reconnect Web Dashboard (Gerardo): Real-time crew map view with location pins Work order board (unassigned, in-progress, completed) Crew utilization and productivity metrics Incident & compliance tracker Cost allocation (labor + equipment by site) Geo-Fencing: Define site boundaries Auto check-in when crew arrives, check-out on departure Alert if crew leaves designated area INTEGRATION POINTS ← Land Division: New sites trigger Field work (site prep, inspections) ← Material Procurement: Field supplies (tools, consumables) ordered through Tracy ← Accounting Hub: Labor costs (ADP integration) + equipment costs → GL → Management/Leasing: Field completion triggers leaseback processing (Dylan) SUCCESS METRICS 100% of work orders created in system (no paper dispatch) Real-time crew location within 100ft accuracy Check-in/out captured 95%+ of time Mobile app >99% uptime in field (with offline support) Site completion signed by Gerardo + site rep on every project 3.3 Management/Leasing Module Owner: Dylan Key Processes: Lease structuring, tenant management, rent collection, property accounting, RealPage integration CONTEXT & CRITICALITY Largest portfolio in Resortments (most active properties) RealPage/OneSite dependency: Platform manages leases, rent, tenant communications Integration criticality: RealPage API unconfirmed; contingency needed High complexity: Multiple lease types, rent structures, special terms, vendor coordination DATA MODEL Properties/Units: Asset from Land Division, address, unit count, rent roll, amenities Leases: Lease ID, tenant, unit, rent amount, term (start/end), lease type (residential, commercial), special terms Rent Roll: Current tenant, rent amount, rent status (paid, due, past due), lease end date Tenants: Contact info, credit, signed documents, move-in/move-out dates Maintenance Requests: Tenant request, description, priority, assigned vendor, completion status Financials: Monthly rent collected, vacancy rates, occupancy %, maintenance costs, net operating income (NOI) WORKFLOWS New Property Leaseback: Received from Legal Close Land → Create property in RealPage/Resortments → Marketing Lease Execution: Prospect identified → Lease drafted (DocuSign) → Signed → Tenant move-in Rent Collection: Monthly rent due → Tenant payment → Reconcile to GL Maintenance: Tenant request → Dylan assigns vendor → Vendor completes → Invoice matches to GL Turnover: Tenant move-out → Lease ends → Unit inspected → Unit prepared → Ready for next tenant FEATURES Property Dashboard: Portfolio overview, occupancy rate, rent roll status, YTD financials Lease Management: Master lease list, lease expiration alerts, renewal tracking Rent Roll: Real-time rent status (paid, due, past-due), aging, collection rate Tenant Portal: View lease, pay rent, submit maintenance requests (Phase 4) Maintenance Tracker: Request → Assignment → Completion, linked to vendor invoices Financials: Monthly NOI calculation, variance from budget, comparison period-over-period RealPage Sync: Bi-directional sync of leases, rent, tenants, maintenance (if API available) REALPAGE INTEGRATION CHALLENGE Current State: API access unconfirmed; platform is critical to Dylan's operations MVP Approach (Phase 3): RealPage as source-of-truth; Resortments mirrors data (one-way read) Phase 4+ Goal: Bi-directional sync if API confirmed Fallback: Manual upload of rent roll CSV daily if no API INTEGRATION POINTS ← Legal Close Land: New properties from David's closings ← Field Division: Maintenance requests from Gerardo's team ← Material Procurement: Maintenance supplies (paint, fixtures) ordered through Tracy ← Accounting Hub: Rent revenue, NOI calculation, lease accounting SUCCESS METRICS 100% of leases tracked in system Rent collection tracked to GL daily RealPage sync (if available): <5% daily failure rate Maintenance requests routed to field within 24 hours Vacancy rate tracked in real-time 3.4 Legal Rollovers Module Owner: David Key Processes: Post-closing tax filings, entity management, annual compliance filings, document retention CONTEXT & SCOPE Lightweight compared to Legal Close Land Mostly integrations: RealPage lookup, filing calendars, document linking David availability: Works alongside his Legal Close Land responsibilities Rollover period management: Tax year, annual renewals, multi-year tracking DATA MODEL Closed Properties: Cross-reference to Legal Close Land closings Tax Filings: Form type (1099-NEC, K-1, partnership return), due date, status (draft, filed, confirmed) Entity Compliance: Annual report, franchise tax, commercial license renewals Document Storage: Closing docs, tax docs, entity filings, retention schedule WORKFLOWS Annual Rollover: Year-end → Due dates calculated → Notifications → David prepares filings Filing Submission: Prepared filing → Submitted to agency → Confirmation tracked Compliance Calendar: System flags due dates 30/15/7 days in advance FEATURES Compliance Calendar: All due dates by entity, jurisdiction, document type Filing Status Tracker: Draft → Submitted → Confirmed with filing receipt Tax Return Linkage: Tie filing to closed properties, supporting docs attached Document Archive: Long-term storage, 10-year retention for audit SUCCESS METRICS Zero missed filing deadlines All tax filings tracked from preparation through confirmation Document retention compliant with 10-year requirements Phase 3 Dependencies & Sequencing Inputs from Phase 2 (must be stable before Phase 3 kickoff): Land Division (Phase 1 pilot, hardened), Legal Close Land, Material Procurement, ADP integration, DocuSign integration. Phase 3 modules and owners: MODULE DIVISION DEPENDS ON FEEDS INTO Material Procurement (equipment Field Division (production handoff), + inventory) Management/Leasing (unit availability) Plant Division (production Management/Leasing (delivery schedule), Land Division (site data) completion → unit ready to lease) Field Division (unit ready), RealPage Legal Rollovers (renewal/eviction one-way read triggers) David Management/Leasing (lease Phase 4 Owner Dashboard reporting McDaniel lifecycle data) OWNER Plant Division Field Division Management / Zac Gerardo Dylan Leasing Legal Rollovers Outputs to Phase 4: All 8 division modules operational in production. Phase 4 layers mobile apps (Field, Plant, Management), advanced RealPage integration, and the Owner Dashboard on top of the nowcomplete platform. Phase 3 Deliverables Plant Division module with full asset tracking and maintenance scheduling Field Division mobile app (iOS/Android) with geo-tracking, time clock, offline support Management/Leasing module with full rent roll and RealPage integration (one-way, at minimum) Legal Rollovers compliance calendar and filing tracker All 8 divisions operational in platform Cross-divisional workflows automated end-to-end Mobile workforce (Field) productive in field (>95% uptime) Milestone: All 8 Divisions Live ✓ Gate Criteria: - All 8 division modules in production - Field Division mobile app live with 90%+ field adoption - RealPage data flowing (one-way minimum) - Plant Division tracking all assets and maintenance - Legal Rollovers meeting all compliance deadlines - Cross-division workflows automated, zero manual handoffs - Russ has complete visibility across all divisions - All 40 users trained and productive Phase 4: Mobile + Advanced Features Timeline: April – June 2027 (3 months) Go-Live: End of June 2027 Payment: - $490,000 released on Phase 4 completion / UAT sign-off (acceptance of Phase 4 deliverables) - $470,000 released on production golive + 30-day stabilization (no unresolved Severity 1 incidents open >24h) - $140,000 retention released 60 days after go-live (final acceptance) Owner: Webaroo Mobile Team, Product & Engineering Dependencies: Phase 3 complete, all divisions stable 4.1 Native Mobile Apps (iOS & Android) Focus: Field operations, real-time connectivity, offline-first design CORE FEATURES (BOTH PLATFORMS) Work Order Management View assigned work orders with directions Real-time location updates (geo-fencing integration) Check-in/check-out with time clock Photo/video capture with annotations Material & tool logging Signature capture (customer sign-off) Inventory Access View available tools/equipment Log tool usage, damage, maintenance Barcode scanning for asset tracking Time Tracking Daily time log, break tracking Overtime calculation Project allocation Documents View work order documents, drawings, specifications Mark up in-app (PDF annotation) Download for offline reference Communication Two-way messaging with Gerardo/manager Photo/video attachments Real-time notifications Offline Mode Full work order access without connectivity Data sync on reconnection Conflict resolution for overlapping edits IOS APP SPECIFICS Target: iPhone + iPad (multi-device login) Deployment: Apple App Store Tech Stack: React Native or native Swift Requirements: iOS 14+, iPhone storage >100MB free ANDROID APP SPECIFICS Target: Android phones and tablets Deployment: Google Play Store Tech Stack: React Native or native Kotlin Requirements: Android 9+, 100MB free storage LAUNCH METRICS Both apps in respective app stores 35+ field users active on mobile (95% of field team) i 99% uptime in field (with offline support) Completion signature capture 100% digital (zero paper) Crew productivity increase 15%+ vs. manual processes 4.2 Advanced Reporting & Analytics Audience: Russ (owner), CFO, division leads, board EXECUTIVE DASHBOARD KPI Cards: Revenue, cost, margin, cash flow, ROI by division Trend Charts: 12-month rolling, year-over-year comparison Heatmaps: Property performance, crew utilization, project profitability Drill-Down Capability: Click any metric to see underlying data Custom Reports: Saved filters, export to Excel, PDF generation OPERATIONAL REPORTS Project Profitability: Budget vs. actual, margin by project Cost Analysis: Spend by vendor, category, time period Cash Flow Forecast: 12-month projection, scenario analysis Utilization Reports: Crew hours, equipment usage, asset availability Compliance Reports: Safety incidents, audit trails, document retention verification AD-HOC QUERY TOOL Data Warehouse: All transactional data (read-only) Query Builder: Non-technical users can create custom reports Saved Queries: Reusable report templates Scheduled Reports: Auto-delivery to email on cadence (daily, weekly, monthly) 4.3 NLP Data Agent (Dylan's Request) i Out of Phase 4 core scope — candidate for Phase 5 Optimization or separate SOW. Not in Charter scope; preserved here to document the product vision. Goal: Natural language queries against enterprise data; "Ask the system anything" CAPABILITIES Natural Language Queries: "What was our rent collection rate last month?" "Which sites are over budget?" "Show me all pending maintenance requests by priority." Intent Recognition: System determines query type (financial, operational, compliance, etc.) Answer Generation: Pulls data, formats response, provides sources Follow-Up Support: "Tell me more", drill-down to underlying data IMPLEMENTATION APPROACH LLM Integration: OpenAI GPT, Anthropic Claude, or on-premise LLM Query Parsing: Map natural language → SQL/GraphQL query Safety Controls: Enforce user permissions (don't expose data they can't see) Audit Trail: Log all queries for compliance Feedback Loop: User corrects misinterpretations to improve accuracy MVP SCOPE Financial queries: Revenue, costs, margins, cash flow Operational queries: Project status, crew location, work orders Compliance queries: Document status, retention, filing dates Supported Responses: Tables, charts, text summaries 4.4 Additional Integrations (Vendor Portals) i Out of Phase 4 core scope — candidate for Phase 5 Optimization or separate SOW. Not in Charter scope; preserved here to document the product vision. Scope: Self-service vendor interfaces for procurement and service delivery MATERIAL PROCUREMENT VENDOR PORTAL Vendor Access: Login with unique credentials PO Visibility: View assigned POs, specifications, delivery schedules Delivery Notification: Upload proof of delivery, photos, signatures Invoice Submission: Digital invoice submission (with PO auto-matching) Communication: Two-way messaging with Tracy Feedback: Performance ratings, issue resolution SERVICE VENDOR PORTAL (FIELD, MAINTENANCE) Work Order Assignment: View assigned work orders with full details Completion Tracking: Mark tasks complete, submit photos, notes Invoice Submission: Submit work invoices against completed orders Communication: Real-time messaging with Gerardo/Dylan COMPSYS INTEGRATION Purpose: Compliance data aggregation (permits, inspections, regulatory filings) Data Flow: Inbound — sync compliance status, notices, violations Use Case: Alerting Russ to regulatory issues, audit trail for inspections HELLO DATA INTEGRATION i Deferred — Phase 5 candidate. Removed from Phase 4 core deliverables per Charter. Purpose: Data analytics partner (future advanced analytics) Data Flow: Read-only access to transactional data for warehousing/BI Use Case: Third-party analysis, benchmarking, industry comparison TREASURY INTEGRATION (FINANCE) i Out of Phase 4 core scope — candidate for Phase 5 Optimization or separate SOW. Not in Charter scope. Purpose: Cash management, payment processing, reconciliation Data Flow: Payment submission, reconciliation, multi-currency support (if applicable) Use Case: Centralized payment hub, treasury reporting Phase 4 Deliverables iOS app in Apple App Store, 100+ downloads Android app in Google Play Store, 100+ downloads Mobile adoption 95% of field team within 30 days Executive dashboard with all KPIs and drill-down Operational reporting library (20+ standard reports) NLP data agent — out of Phase 4 core scope (Phase 5 / separate SOW candidate) Vendor portal — out of Phase 4 core scope (Phase 5 / separate SOW candidate) Compsys integration syncing daily (Hello Data and Treasury deferred — Phase 5 candidates) Milestone: Full Platform with Mobile ✓ Gate Criteria: - Mobile apps live and widely adopted (90%+ field team) - Advanced reporting reducing manual report generation by 80% - NLP agent (if pulled forward via separate SOW) enabling self-service analytics — otherwise deferred to Phase 5 - Vendor portals (if pulled forward via separate SOW) reducing admin overhead — otherwise deferred to Phase 5 - In-scope integrations stable and daily-syncing (Hello Data / Treasury deferred) - Platform achieving target SLAs: 99.5% web uptime, 99% mobile uptime - User satisfaction >4/5 across all divisions Phase 5: Optimization & Maturity Timeline: July 2027+ (ongoing; Phase 5 absorbs NLP Data Agent, Vendor Portals, Hello Data, and Treasury Integration deferred from Phase 4) Owner: Webaroo + Resortments IT team Dependencies: Phase 4 complete, platform production-ready 5.1 AI & Intelligent Automation Features Document Intelligence: Auto-parsing of uploaded invoices, contracts, permits Entity extraction (vendor names, amounts, due dates) Classification (receipt, invoice, permit, license) Language model tagging and categorization Blocker Detection: Predictive analytics on project delays Risk flagging (cost overruns, schedule slips) Recommendation engine (propose corrective actions) Predictive Analytics: Forecast cash flow based on historical patterns Predict rent collection risk by tenant Maintenance need prediction (equipment failure forecasting) Intelligent Routing: Auto-assign work orders based on crew skills & location Dynamic crew scheduling optimization Load balancing across Field teams 5.2 External Vendor/Contractor Portal Self-Onboarding: Vendors register, submit credentials, insurance, W-9 Job Marketplace: Browse available work, submit bids, track assigned projects Communication Hub: Project messaging, document exchange Performance Tracking: Ratings, reviews, repeat business optimization Payment & 1099 Reporting: Self-service invoice submission, payment tracking, 1099 generation 5.3 Performance & Scalability Optimization Database Tuning: Index optimization for large tables (Material Procurement, Leasing) Partitioning for historical data (7-year archive) Query performance monitoring and optimization Caching Strategy: Redis caching for frequently accessed data (property lists, user profiles) CDN for static assets (photos, documents) Intelligent cache invalidation Mobile Optimization: App size reduction, lazy loading Compressed photo/video transmission Battery optimization for continuous geo-tracking Infrastructure Scaling: Load balancing across API servers Database replica for read-heavy reporting Auto-scaling for seasonal peaks (summer construction season) 5.4 Advanced Automation & Workflow Rules Rules Engine: Conditional workflows (If cost > $10K, then require VP approval) Multi-step approval chains with escalation Automated reassignment on user unavailability Integration Workflows: Bi-directional syncs with advanced conflict resolution Scheduled batch operations (nightly reconciliation, weekly close) Error handling and retry logic External Triggers: Webhook support from third-party systems (RealPage events, ADP payroll runs) Email-triggered actions (invoice from new vendor) Time-based triggers (monthly close, quarterly reporting) 5.5 Continuous Improvement & Support User Feedback Loop: In-app feature request voting NPS surveys and usability testing Monthly product updates based on usage analytics Training & Enablement: Role-based training materials (video, docs, interactive guides) New user onboarding certification Monthly lunch-and-learns with product team Maintenance & SLA Management: 99.95% uptime SLA commitment Monitored incident response <1 hour for critical issues Quarterly security audits Annual disaster recovery testing Phase 5 Success Metrics Platform uptime 99.95%+ consistently Document parsing accuracy 95%+ Blocker detection preventing 80%+ of schedule delays Vendor portal adoption 100% of active vendors User satisfaction maintaining >4.2/5 NPS Stretch goal: measurable cost reduction per division, baseline established in Phase 1 discovery Time-to-decision reduced by 50%+ via NLP agent and analytics Milestone Summary & Timeline PHASE START END DURATION KEY MILESTONE Phase 0 — Scoping Mar 15, Apr 30, 6.5 weeks Discovery Complete (Apr 30, 2026) 2026 2026 May 1, 2026 Aug 31, 4 months MVP Launch (Aug 31, 2026) 4 months Wave 1 Live (Dec 31, 2026) 3 months All 8 Divisions Live (Mar 31, 2027) 3 months Go-Live: Mobile + Advanced (Jun 30, Phase 1 — Foundation / MVP 2026 Phase 2 — Wave 1 Sep 1, 2026 Dec 31, 2026 Phase 3 — Wave 2 Jan 1, 2027 Mar 31, 2027 Phase 4 — Mobile + Apr 1, 2027 Advanced Jun 30, 2027 Phase 5 — Optimization Jul 1, 2027 Ongoing 2027) Continuous Steady-state operation & enhancements PHASE TIMELINE KEY OUTCOME OWNER STATUS 0: Scoping Mar – Apr 2026 Formal scope, architecture, resource plan Russ + In Progress Webaroo 1: MVP May – Aug 2026 Russ logs in, sees unified data (4 mo) 2: Wave 1 Sep – Dec 2026 Land, Legal, Procurement, Integrations live (4 mo) 3: Wave 2 Jan – Mar 2027 Plant, Field, Leasing, Rollovers live (3 mo) 4: Mobile 5: Webaroo Pending Eng kickoff Webaroo Pending Eng Phase 1 Webaroo Pending Eng Phase 2 Apr – Jun 2027 iOS/Android, Executive dashboard, go-live Webaroo Pending (3 mo) end of June 2027 Eng Phase 3 Jul 2027+ AI, NLP agent, Vendor portals, Hello Data, Webaroo + Ongoing Treasury, Performance tuning IT Optimization Key Dependencies & Risk Mitigation Critical Path Dependencies 1. Phase 1 → Phase 2: MVP foundation stable (Auth, DB, API, Acct Hub) before Wave 1 2. Phase 2 → Phase 3: Land + Legal Close stable before Field/Leasing operational 3. RealPage API: Unconfirmed; Leasing module contingency = CSV upload if API unavailable 4. Accounting Hub Interview: Complete (April 8, 2026); financial data model confirmed 5. DocuSign Scale: 10,000 envelopes/year; load testing critical before Phase 2 production Decision Gates (Approval Required to Proceed) End of Phase 0: Scope signed off by Russ + Leadership (decision point: Full platform vs. phased) End of Phase 1: MVP stable for 2 weeks (decision point: Proceed to Wave 1 on schedule) End of Phase 2: Wave 1 divisions profitable within platform (decision point: Pause for optimization vs. proceed to Wave 2) RealPage API Decision: Q2 2026 (decision point: Invest in bi-directional sync vs. CSV fallback) Mobile Launch Decision: Q2 2027 (decision point: Immediate full launch vs. beta with select crew) Risk Mitigation Summary RISK MITIGATION OWNER RealPage API unconfirmed Design Leasing module with CSV fallback; test integration by Webaroo Eng Q1 2027 Accounting Hub scope Complete interview Q2 2026; add financial lead to core team Russ DocuSign scale (10K Load testing 500/day in Phase 2; queue management + Webaroo Eng envelopes) exponential backoff Plant doesn't exist yet Design modular asset tracking; validate with Zac monthly Zac + Webaroo during Phase 3 Eng Data digitization (Dallas Budget OCR service; begin scanning Q2 2026 for Phase 1 Russ + Finance invoices) testing Change management (8 Assign division champions; monthly training + support; divisions) measure adoption metrics Key person dependency Document all decision-making; create wiki of business rules; (Russ) groom backup owner unclear Webaroo PM Russ + PM Resource & Team Structure Webaroo Core Team (Estimated FTE) ROLE PHASE 0 PHASE 1 PHASE 2 PHASE 3 PHASE 4 PHASE 5 Product Manager 0.5 1.0 1.0 1.0 1.0 0.5 Engineering Lead 0.5 1.0 1.0 1.0 1.0 0.5 Full-Stack Engineers 1.0 4.0 4.0 3.0 2.0 2.0 Mobile Developers — — — 0.5 2.0 1.0 QA / Test 0.5 1.5 1.5 1.5 1.0 0.5 DevOps / Infra 0.5 1.0 1.0 1.0 0.5 0.5 Designer / UX 0.5 1.0 1.0 0.5 1.0 0.5 Data / Analytics — — 0.5 0.5 1.0 1.0 Total Webaroo FTE 3.5 10.0 10.5 9.5 8.5 6.0 Resortments Stakeholder Engagement DIVISION KEY STAKEHOLDER ROLE IN DELIVERY AVAILABILITY Owner Russ Project sponsor, approvals, vision High Finance Johnny CPA (Accounting Accounting Hub owner, GL mapping Medium Lead) Land Russ (Owner) Module champion, data source High Legal Close David Module champion, DocuSign config Medium Procurement Tracy Module champion, vendor High management Plant Zac Future asset owner, maintenance Low (ramps up Phase planning 3) Field Gerardo Mobile champion, crew logistics Medium Leasing Dylan RealPage liaison, module champion High Success Criteria & Acceptance Phase 0 Complete All 8 division stakeholder interviews complete Formal Scope of Work document signed by Russ (Owner/Executive) + Johnny CPA (Accounting Lead) Architecture & tech stack approved by Webaroo + IT Budget & resource plan approved Phase 1 backlog refined and estimated Team fully assembled and onboarded Phase 1 Complete 40 users can log in with SSO + 2FA Owner Dashboard accessible with unified data view Accounting Hub syncing QB data reliably Document management storing 10GB per user Basic workflows triggering correctly Security audit passed (zero critical, <3 high severity findings) 2-week production stability achieved (99.5% uptime) Phase 2 Complete Land module tracking all active properties with real-time costs Legal Close Land automating closings via DocuSign Material Procurement handling 2000+ annual POs ADP sync 100% accurate (payroll costs to GL) DocuSign handling 500+ envelopes/month peak Cross-divisional workflows automated (Land → Legal, → Material) Russ + David + Tracy fully operational in system Finance able to close books using platform data Phase 3 Complete All 8 divisions operational and profitable within platform Field Division mobile app >95% adoption by crew Plant module tracking all assets and maintenance Leasing module managing rent roll with RealPage sync Legal Rollovers meeting 100% of compliance filing deadlines Cross-division workflows fully automated, zero manual handoffs Russ has complete visibility + ability to drill-down into any data All 40 users trained and self-sufficient Phase 4 Complete iOS and Android apps in app stores (combined 200+ downloads) Field crew productivity increased 15%+ vs. paper processes Executive dashboard replacing 80% of manual reporting NLP agent responding to queries with 90%+ accuracy Vendor portals live with 50%+ vendor adoption All integrations (Compsys, Hello Data, Treasury) syncing daily Phase 5 Ongoing 99.95% uptime SLA maintained Document parsing 95%+ accurate User satisfaction (NPS) >4.2/5 Stretch goal: measurable cost reduction per division, baseline established in Phase 1 discovery Platform supporting future expansion to 15+ divisions Assumptions & Constraints Assumptions 1. Accounting Hub Interview: Scheduled and completed by end of April 2026 2. RealPage API: Confirmation of access and data availability by Q2 2026 3. QuickBooks Data: Can be read via QB API; no complex migration needed 4. Team Availability: Webaroo team 100% dedicated; no context-switching 5. Division Cooperation: Stakeholders provide timely feedback and UAT participation 6. Budget: Approved at $2.6M–$3.0M for 14-month build + Year 1 support, payable on a milestone schedule with $300K collected upfront for Phase 1. See Budget Estimate for full payment schedule. 7. Data Quality: Historical data can be manually entered or imported by divisions Constraints Timeline: Aggressive 14-month schedule; no phase compression without resource increase Mobile Priority: Field Division requires mobile to be credible; cannot delay past Phase 4 RealPage Dependency: Leasing module blocked if API unavailable; CSV contingency slow Data Fragmentation: No automated way to consolidate data from OneDrive, email, sheets; manual effort required Change Management: 8 divisions with zero tech infrastructure; training & adoption risk high Compliance: 7-10 year retention + regulatory tracking (OSHA, IPIA, Fair Housing) must be built in from start Document Information Author: Webaroo Project Team Prepared For: Russ (Owner), Resortments Leadership Last Updated: April 2026 Version: Final Next Review: 2026-05-01 (Phase 0 completion) Approval: ___ (Sponsor) ____ (Date) This roadmap is a living document. Updates will be published monthly as the project progresses through phases. All milestone dates are targets and subject to resource availability and scope confirmation. NAVIGATE THE PACKAGE All Discovery Materials 01 Audit & Competitor Analysis 02 Technical & Project Evaluation 03 Project Charter 04 Project Roadmap & Milestones 05 Risk Analysis & Mitigation 06 Budget Estimate 07 Product Backlog 08 Payment Schedule & Terms