Tax Organizer for Personal & Consultant

Organizes and processes personal tax documents to generate accurate, tax reports and drafts. Use when user uploads or describes tax forms (W-2, 1099s, K-1s, 1098), mentions rental properties, royalties, partnerships/S-corps, business expenses, donations, or needs Schedule E drafts. Handles complex income sources, expense matching, per diem optimization, and charitable receipt identification.

When to Use

• Organizing personal and consultant tax documents
• Processing rental property expenses, income, and depreciation
• Matching business trip expenses with per diem optimization
• Generating tax-ready XLS reports for accountant review
• Classifying W-2s, 1099s, and donation receipts
• Tracking incremental document additions across multiple sessions

Usage

Navigate to your tax year folder and run this skill.
Drop documents anytime — the skill detects new files and only processes what's changed.

Folder Structure

The skill expects and creates this layout in the working directory:

Tax-2025/
├── README.md                     # Global config + instructions
├── Rental-123-Main-St/
│   ├── README.md                 # Business config (see template below)
│   └── (drop receipts/invoices here)
├── Freelance-Consulting/
│   ├── README.md
│   └── ...
├── W2s/                          # W-2 forms
├── 1099s/                        # All 1099 variants
├── Donations/                    # Charitable contribution receipts
├── Unclassified/                 # Files the skill couldn't classify
├── Reports/                      # Generated XLS outputs
└── .processed-files.log          # Internal: tracks processed files

Special folders

• W2s/ — W-2 forms. Organized for reference (Form 1040, not Schedule E).
• 1099s/ — All 1099 variants (NEC, MISC, INT, DIV, K-1, etc.).
• Donations/ — Charitable contribution receipts (Form 8283 / Schedule A).
• Unclassified/ — Documents that couldn't be auto-classified. Flagged for manual review.
• Reports/ — Generated XLS report files. Regenerated on every run.

Root README.md Template

When no root README.md exists, generate one from this template (fill in from user responses):

# Tax Documents — {{TAX_YEAR}}

## Instructions

This folder organizes your tax documents for the {{TAX_YEAR}} tax year.

### How to use

1. **Drop receipts and documents** into the tax year folder
   — or into any existing business subfolder
2. **Run the skill** — it scans your documents, identifies business
   lines, and guides you through setup
3. **Add more documents anytime** — the skill detects new files and
   only processes what's changed

### Special folders

- `W2s/` — Drop W-2 forms here (organized for reference)
- `1099s/` — Drop all 1099 forms here
- `Donations/` — Drop charitable contribution receipts here

## Filing Information

- **Tax Year**: {{TAX_YEAR}}
- **Filing Status**: {{FILING_STATUS}}
- **Preparer**: {{PREPARER_NAME}}

Business README.md Template

Each business folder gets a README.md that serves as both config and documentation. Generate from this template:

# {{BUSINESS_NAME}}

## Business Information

- **Type**: {{BUSINESS_TYPE}}
- **EIN**: {{EIN}}
- **Address**: {{ADDRESS}}
- **Ownership**: {{OWNERSHIP_PERCENTAGE}}%

## Property Details

<!-- Only for rental properties -->

- **In-Service Date**: {{IN_SERVICE_DATE}}
- **Cost Basis**: ${{COST_BASIS}}
- **Land Value**: ${{LAND_VALUE}}
- **Depreciation Method**: {{DEPRECIATION_METHOD}}

## Business Trips

<!-- List trips related to this business. The skill will auto-match
     expenses (flights, hotels, meals, taxi, conference fees) that
     fall within these date ranges. -->

### {{TRIP_NAME}} — {{TRIP_DESTINATION}}

- **Dates**: {{TRIP_START}} – {{TRIP_END}}
- **Purpose**: {{TRIP_PURPOSE}}

## Important Events

<!-- Note major events that affect tax treatment -->

- **{{EVENT_DATE}}**: {{EVENT_DESCRIPTION}}

## Notes

<!-- Any additional notes for your records or your accountant -->

Business types: Residential Rental, Commercial Rental, Royalties, Partnership (K-1), S-Corp (K-1), Freelance/Self-Employment, Farm Rental

Depreciation methods:

• Residential rental: Straight-line over 27.5 years
• Commercial rental: Straight-line over 39 years
• Include mid-month convention for the placed-in-service year

Incremental Processing

The skill maintains a .processed-files.log in the root folder to track what has been processed:

# Tax Organizer — Processed Files Log
# Format: SHA256_HASH | ORIGINAL_PATH | ORGANIZED_PATH | TIMESTAMP
a1b2c3d4... | ./invoice_march.pdf | ./Rental-123-Main-St/2024-03-15 Plumber Co - Repairs - Pipe fix.pdf | 2024-12-01T10:30:00
e5f6g7h8... | ./receipt.jpg | ./Rental-123-Main-St/2024-04-20 Home Depot - Supplies - Door hardware.jpg | 2024-12-01T10:30:00

Processing rules

On each run, hash all files in the directory tree (excluding Reports/ and the log itself), then compare against .processed-files.log:

Report to user: "Found X new files, Y duplicates, Z already processed"

Workflow

Execute these 9 steps in order:

Step 1: Scan & Discover

1. Scan the working directory recursively for all documents: PDF, JPG, PNG, JPEG, TIFF, XLS, XLSX, CSV, EML, MSG. For XLS/XLSX files, use the /xlsx skill to read their contents.
2. Exclude Reports/ folder and .processed-files.log
3. Compute SHA-256 hash for each file found
4. Load .processed-files.log if it exists
5. Categorize every file as: new, already-processed, duplicate, or moved/renamed (see Processing Rules above, use mv instead of cp)
6. Detect existing README.md configs in business folders
7. Report to user:
   • Total files found
   • New files to process
   • Duplicates found
   • Already processed (skipped)
   • File types breakdown

If there are zero new files to process, skip to Step 8 (regenerate reports) or inform the user and stop.

Step 2: Interactive Business Setup

First run (no root README.md found):

1. Ask user for:
   • Tax year
   • Filing status (Single, Married Filing Jointly, Married Filing Separately, Head of Household, Qualifying Surviving Spouse)
   • Preparer name (their name or accountant's name)
2. Generate the root README.md using the template above
3. Create empty special folders: W2s/, 1099s/, Donations/, Unclassified/, Reports/
4. Analyze the new documents found in Step 1 and identify likely business lines:
   • Property addresses on invoices/receipts → suggest a rental or commercial property folder
   • Payer names on 1099-NEC/MISC → suggest a freelance or royalty folder
   • K-1 forms → suggest a Partnership or S-Corp folder
   • Group documents that share an address or entity name into a single proposed business
5. Present the suggested business lines to the user, for example:

   I found documents referencing these potential business lines:
   
   1. "456 Oak Ave" — appears on 3 receipts and a 1098. Looks like a rental property.
   2. "Acme Consulting LLC" — appears on a 1099-NEC. Looks like freelance income.
   
   For each one I'll ask a few questions to set it up.
   

6. For each confirmed business line, ask:
   • Business name (suggest one based on address or entity name)
   • Business type (Residential Rental, Commercial Rental, Royalties, Partnership, S-Corp, Freelance/Self-Employment, Farm