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Ashfolio Roadmap: v0.6.0 - v1.0 (Professional-Grade Financial Platform)

Local-first, single-user, SQLite-based comprehensive financial management platform

Updated: November 2025 (Current: v0.10.0) | Based on CFP/CPA Professional Assessment

Transform Ashfolio from comprehensive personal finance tool to professional-grade platform meeting fiduciary and regulatory standards.

Current State: v0.10.0 ✅ COMPLETED

Delivered Features (Through v0.10.0)

  • Portfolio Management: FIFO cost basis tracking with multi-account support
  • Tax Planning: Capital gains analysis, tax-loss harvesting opportunities
  • Money Ratios: Charles Farrell's 8-ratio financial health assessment
  • Retirement Planning: 25x rule, 4% SWR, Monte Carlo projections
  • Expense Analytics: Complete tracking with categorization and trends
  • Financial Goals: Emergency fund, retirement, custom savings goals
  • Performance Analytics: TWR/MWR calculations with benchmarking
  • Advanced Analytics: Efficient frontier, portfolio optimization, risk metrics
  • AI Natural Language Entry: Ollama/OpenAI support for transaction parsing
  • MCP Integration: Privacy-filtered AI assistant portfolio access
  • AI Consent Management: GDPR-compliant consent and privacy controls
  • Architecture: 2,200+ tests, Decimal precision, ETS caching, PubSub updates

Professional Assessment Score: A- (Exceptional for v0.10)

v0.6.0: Professional Standards & Tax Accuracy 🎯

Q4 2025 - Q1 2026 (12 weeks) Priority: Features required for professional financial advisory use

Phase 1: Tax Accuracy & Compliance (Weeks 1-4) 🏆 HIGHEST PRIORITY

Corporate Actions Engine (Score: 94/100)

Why Critical: #1 source of tax reporting errors and amended returns

  • Stock Splits - Forward/reverse with automatic basis adjustment
  • Dividends - Cash/stock/special with qualified status tracking
  • Mergers & Acquisitions - Symbol conversion, cash/stock consideration
  • Spin-offs - Cost basis allocation per IRS guidelines
  • Return of Capital - Basis reduction tracking
  • Capital Distributions - Proper gain/loss recognition

Acceptance Criteria:

  • All adjustments maintain FIFO ordering
  • Historical transactions show adjustment notes
  • Total portfolio value unchanged by splits
  • Qualified dividend identification for tax rates

Tax Document Generation (Score: 92/100) 🆕

Why Critical: IRS compliance and audit defense

  • Schedule D Export - Capital gains/losses in IRS format
  • Form 8949 - Detailed transaction reporting with adjustments
  • 1099-B Reconciliation - Match broker reported basis
  • State Tax Reports - Multi-state capital gains allocation
  • Tax Loss Harvesting Report - Wash sale adjusted opportunities
  • Estimated Tax Calculator - Quarterly payment optimization

Acceptance Criteria:

  • Export formats match IRS specifications
  • Wash sale adjustments properly calculated
  • State allocation based on residence dates
  • PDF and CSV export options

Phase 2: Fiduciary Compliance (Weeks 5-8)

Risk Analytics Suite (Score: 78/100)

Why Critical: Required for Investment Policy Statements and fiduciary duty

  • Sharpe Ratio - Risk-adjusted return measurement
  • Sortino Ratio - Downside deviation focus
  • Information Ratio - Active management assessment
  • Maximum Drawdown - Peak-to-trough analysis
  • Value at Risk (VaR) - 95% confidence interval
  • Beta & Correlation - Systematic risk measurement
  • Standard Deviation - Volatility tracking

Acceptance Criteria:

  • All calculations use daily returns
  • Minimum 3-year history for validity
  • Cache results for performance
  • Export for IPS documentation

Portfolio Optimization Engine (Score: 76/100)

Why Critical: Professional portfolio management standard

  • Tax-Aware Rebalancing - Minimize realized gains
  • Asset Location Optimizer - Tax-efficient placement
  • Rebalancing Bands - Threshold-based triggers
  • Trade Optimization - Minimize transaction costs
  • Tax Budget Setting - Annual gain/loss targets
  • Loss Harvesting Integration - Coordinated tax strategy

Acceptance Criteria:

  • Consider wash sale rules
  • Account for transaction costs
  • Generate rebalancing orders
  • Estimate tax impact before execution

Phase 3: Advanced Planning Tools (Weeks 9-12)

Required Minimum Distributions (RMD) 🆕

Why Critical: SECURE Act 2.0 compliance, avoiding 50% penalty

  • RMD Calculator - Age-based requirements
  • Inherited IRA Rules - 10-year rule tracking
  • QCD Optimization - Qualified Charitable Distributions
  • Multiple Account Aggregation - Satisfy from any IRA
  • Roth Exclusion - Proper account type handling
  • Penalty Tracker - Missed RMD warnings

Acceptance Criteria:

  • SECURE Act 2.0 rules (age 73+)
  • Uniform lifetime table accuracy
  • Multi-beneficiary calculations
  • Year-end deadline alerts

Roth Conversion Optimizer 🆕

Why Critical: Multi-year tax planning optimization

  • Tax Bracket Analysis - Fill lower brackets
  • IRMAA Cliff Awareness - Medicare premium impacts
  • Multi-Year Planning - 5-10 year optimization
  • State Tax Consideration - Relocation planning
  • Recharacterization Tracking - Undo conversions
  • Pro-Rata Rule - IRA basis tracking

Acceptance Criteria:

  • Current year tax projection
  • Medicare surcharge thresholds
  • State tax differential analysis
  • Conversion ladder planning

v0.7.0: Advanced Portfolio Analytics ✅ COMPLETE

Released: September 21, 2025 Focus: Professional-grade portfolio analytics and optimization

Status: 100% Complete

  • Stage 1: Risk Metrics (Beta, Drawdown, Calmar, Sterling) ✅ Complete
  • Stage 2: Correlation & Covariance Matrices ✅ Complete
  • Stage 3: Portfolio Optimization (Efficient Frontier) ✅ Complete
  • Stage 4: Advanced Analytics LiveView ✅ Complete

Completed Features ✅

Advanced Risk Metrics ✅

  • Beta Calculator - Systematic risk vs market (20 tests passing)
  • Drawdown Calculator - Maximum loss and recovery tracking (24 tests)
  • Enhanced Risk Metrics - Added Calmar & Sterling ratios (13 new tests)
  • Performance: All calculations < 100ms requirement met

Correlation & Covariance Analysis ✅

  • Correlation Calculator - Pearson correlation, matrices, rolling windows (27 tests)
  • Covariance Calculator - Pairwise and matrix calculations (16 tests)
  • Full Decimal precision throughout
  • Newton's method for square root calculations

Portfolio Optimization Engine ✅

  • Efficient Frontier - Complete Markowitz optimization with analytical solutions
  • N-Asset Tangency Portfolio - Approximation algorithm with 99% accuracy
  • Multiple Portfolio Types - Minimum variance, tangency, and maximum return portfolios
  • Interactive Visualization - Color-coded portfolio cards with allocation displays

Advanced Analytics LiveView ✅

  • Interactive Dashboard - Real-time portfolio analytics with sub-second performance
  • Professional UI - Consistent styling with loading states and calculation history
  • Performance Caching - 1-hour TTL with cache statistics display
  • Comprehensive Integration - All calculators unified in single dashboard

v0.8.0: AI Natural Language Entry ✅ COMPLETE

Released: November 25, 2025 Focus: AI-powered transaction entry with local-first privacy

Status: 100% Complete

Completed Features ✅

AI Natural Language Transaction Parsing ✅

  • Natural Language Parsing - "Bought 10 AAPL at 150 yesterday"
  • Transaction Auto-Fill - Extract type, symbol, quantity, price, date
  • Local-First AI (Ollama) - 100% private, runs on your computer
  • Cloud Alternative (OpenAI) - Optional opt-in for quick setup
  • Multi-Provider Support - Extensible dispatcher architecture
  • User Review Required - All AI-parsed data requires manual confirmation
  • Supported Transaction Types - Buy, sell, dividend, deposit, withdrawal, fee, interest

AI Module Architecture ✅

  • Dispatcher Pattern - Routes requests to appropriate AI handlers
  • Handler Behaviour - Standardized interface for AI handlers
  • Transaction Parser - Natural language to structured data
  • Model Configuration - Provider and model selection management
  • Graceful Degradation - Fallback to manual entry when AI unavailable

Strategic Rationale

  • User Alignment: 82% of current user base prefers local AI (technical cohort)
  • Brand Consistency: Reinforces local-first, privacy-first philosophy
  • Differentiation: First financial app with truly local AI integration
  • Extensibility: Dispatcher pattern enables future AI features

v0.9.0: MCP Integration ✅ COMPLETE

Released: November 28, 2025 Focus: AI assistant portfolio access with privacy controls

Status: 100% Complete

Completed Features ✅

Model Context Protocol (MCP) Server ✅

  • MCP 2024-11-05 Specification - Complete implementation
  • Privacy-Filtered Data Access - Configurable privacy modes
  • Four Core Tools - list_accounts, get_portfolio_summary, list_transactions, list_symbols
  • JSON-RPC 2.0 Transport - Over stdio for AI assistant integration

Privacy Filtering System ✅

  • Four Privacy Modes - Strict, anonymized, standard, full
  • Account Anonymization - Names → letters (A, B, C)
  • Amount Tier Masking - $1K-$10K, $10K-$100K ranges
  • Configurable Environment - Application-level privacy settings
  • Deterministic Anonymization - Consistent across requests

AshAi Integration ✅

  • Domain-Level Tools - Ash framework native MCP support
  • Automatic Schema Generation - From Ash resources
  • Type-Safe Execution - Validated tool inputs/outputs

Technical Implementation

  • MCP Router - Initialize, tools/list, tools/call methods
  • Privacy Filter - Mode-aware data transformation
  • Anonymizer - Deterministic letter assignment and tier classification

v0.10.0: MCP Phase 2 - AI Consent & Tool Discovery ✅ COMPLETE

Released: November 30, 2025 Focus: GDPR-compliant consent management and optimized AI context

Status: 100% Complete (123 new tests)

Completed Features ✅

AI Settings Page ✅

  • Consent Management Interface - Complete privacy control dashboard
  • Privacy Mode Selection - Strict, anonymized, standard, full with descriptions
  • Feature Toggles - MCP tools, AI analysis, cloud AI
  • GDPR Data Export - JSON export of consent and audit records
  • Consent Revocation - Immediate withdrawal with audit trail
  • Visual Status Indicators - Clear consent state display

Natural Language Parsing ✅

  • Amount Parser - $100, 85k, EUR 500, ranges ($50-100)
  • Date Parsing - Relative terms (today, yesterday)
  • Two-Phase MCP Tools - Guidance → structured execution
  • Schema-Driven Validation - For expenses and transactions
  • Decimal Precision - Currency-aware parsing

Tool Discovery & Search ✅

  • Module Registry - GenServer for centralized tool discovery
  • Tool Search - Anthropic advanced pattern (~85% token reduction)
  • Privacy-Aware Filtering - Tools filtered by consent mode
  • Runtime Registration - Extensible tool system
  • Keyword Scoring - Intelligent tool matching algorithm

Legal & Consent Infrastructure ✅

  • AiConsent Resource - Versioned terms acceptance
  • ConsentAudit - Append-only audit trail
  • Consent Modal - Feature selection and terms display
  • ConsentCheck Hook - LiveView consent enforcement
  • Terms Versioning - SHA256 hash for detecting changes

Technical Implementation

  • Parsing Module - Parseable behaviour, AmountParser, Schema helpers
  • MCP Infrastructure - ModuleRegistry, ToolSearch, ParserToolExecutor
  • Legal Domain - AiConsent and ConsentAudit resources

v0.11.0: Estate Planning & Advanced Tax Strategies

Q1-Q2 2026 (10 weeks) Focus: Comprehensive wealth transfer and advanced tax planning

Estate Planning Foundation 🆕

  • Beneficiary Management - Primary/contingent tracking
  • Step-Up Basis Modeling - Estate tax planning
  • Gift Tax Tracking - Annual exclusion monitoring
  • Trust Account Support - Revocable/irrevocable basics
  • Inherited Asset Tracking - Basis and date tracking
  • Estate Tax Calculator - Federal/state estimates

Multi-Broker Risk Management 🆕

  • Cross-Broker Wash Sale Alerts - Real-time violation prevention
  • Multi-Account Transaction Coordination - Unified trading view
  • Consolidated Position Tracking - Total exposure across brokers
  • Historical Data Recovery Tools - Reconstruct lost basis from transfers

Alternative Minimum Tax (AMT) 🆕

  • ISO Exercise Planning - Minimize AMT exposure
  • AMT Credit Tracking - Carryforward management
  • Preference Item Analysis - Identify AMT triggers
  • Multi-Year AMT Planning - Strategic timing

Cryptocurrency Tax Compliance 🆕

  • Crypto Cost Basis - FIFO/LIFO/specific ID
  • Mining/Staking Income - Ordinary income tracking
  • DeFi Transaction Import - Yield farming, liquidity
  • NFT Gain/Loss - Collectibles tax rate

v0.12.0: Institutional Features

Q3 2026 (8 weeks) Focus: Features for advisors managing multiple households

Multi-Entity Support

  • Business Accounts - LLC, S-Corp, C-Corp
  • 401(k)/403(b) Integration - Employer plan tracking
  • Equity Compensation - RSU, ISO, ESPP
  • Deferred Compensation - 409A tracking

Advanced Reporting

  • Client Presentation Mode - Professional reports
  • Batch Report Generation - Multiple time periods
  • Custom Report Builder - Drag-and-drop fields
  • Audit Trail - Complete change history

v0.13.0: Integration & Automation

Q4 2026 (6 weeks) Focus: Workflow automation and external integrations

Import/Export Ecosystem

  • TurboTax Integration - Direct tax export
  • Quicken/Mint Import - Migration tools
  • PDF Statement Parser - OCR for statements
  • API Framework - Read-only access

Automation Features

  • Rule-Based Categorization - ML-powered
  • Scheduled Reports - Email delivery
  • Alert System - Rebalancing, RMD, tax
  • Backup Automation - Encrypted backups

v1.0.0: Production Release

Q1 2027 (4 weeks) Focus: Polish, performance, and production readiness

Release Criteria

  • ✅ 2,200+ tests passing (currently met)
  • ✅ 100% critical path coverage
  • ✅ Professional documentation
  • ✅ Performance benchmarks met
  • ✅ Security audit passed
  • ✅ WCAG accessibility compliance
  • ✅ Cross-platform testing complete

Success Metrics

Professional Adoption Metrics

  • CFP/CPA Validation: Features meet professional standards
  • Regulatory Compliance: IRS reporting accuracy 100%
  • Performance Standards: All calculations <100ms
  • Accuracy Standards: Decimal precision, no rounding errors
  • Security Standards: Encrypted local storage

Technical Excellence Metrics

  • Test Coverage: >95% for financial calculations (currently 2,200+ tests)
  • Code Quality: Zero Credo/Dialyzer warnings
  • Performance: <500ms dashboard refresh
  • Reliability: <0.1% error rate in production
  • Documentation: 100% public API documented

Development Principles

Mandatory Requirements

  • ✅ Test-Driven Development (Red-Green-Refactor)
  • ✅ Decimal type for all financial calculations
  • ✅ FIFO cost basis consistency
  • ✅ Local-first architecture maintained
  • ✅ No cloud dependencies added

Quality Gates (Per Feature)

  1. Comprehensive test suite written first
  2. CFP/CPA review of calculations
  3. Performance benchmarks verified
  4. Documentation complete
  5. Integration tests passing

Risk Mitigation

Regulatory Risks

  • Tax Law Changes: Modular tax engine for easy updates
  • State Variations: Configurable state tax rules
  • International: US-focused initially, extensible design

Technical Risks

  • SQLite Scaling: Performance testing at 1M+ transactions
  • Calculation Complexity: ETS caching for expensive operations
  • Data Migration: Comprehensive backup/restore system

Long-Term Vision (Post v1.0)

Potential Expansions

  • Multi-user/family support (major architecture change)
  • Cloud sync option (optional, privacy-preserved)
  • Mobile applications (iOS/Android)
  • International tax support
  • Institutional advisor platform

Maintaining Core Values

  • Local-first remains default
  • Privacy always paramount
  • No vendor lock-in
  • Open source commitment
  • Transparent calculations

This roadmap incorporates professional CFP/CPA assessment feedback to ensure Ashfolio meets the highest standards for financial planning and tax compliance software.

Revision History

  • 2025-11-30: v0.10.0 completed - MCP Phase 2 (AI consent, parsing, tool discovery)
  • 2025-11-28: v0.9.0 completed - MCP Integration (privacy filtering, 4 MCP tools)
  • 2025-11-25: v0.8.0 completed - AI Natural Language Entry (Ollama/OpenAI support)
  • 2025-11-22: v0.8.0 roadmap - AI Natural Language Entry (Phase 1), deferred Estate Planning to v0.11.0
  • 2025-09-22: v0.7.0 completed with full portfolio analytics suite
  • 2025-09-21: v0.7.0 released with advanced portfolio analytics
  • 2025-09-16: v0.7.0 50% complete - Risk metrics and correlation/covariance done
  • 2025-09: Reorganized roadmap to reflect v0.7.0 portfolio analytics focus
  • 2025-09: Added professional assessment features (Tax Docs, RMD, Roth)
  • 2025-09: Prioritized based on CFP/CPA scoring matrix
  • 2025-08: v0.5.0 completed with tax planning
  • 2025-07: v0.4.x delivered advanced analytics
  • 2025-06: Initial roadmap creation