cowork-tax-prep-organizer

Cowork Tax Prep Organizer

Do the part of tax season that actually eats the weekend: finding, identifying, and organizing the documents. Input: one or more folders (Downloads, a documents dump, last year's tax folder for reference). Output: an organized package a CPA can work from and a precise list of what is still missing. This skill organizes; it does not compute taxes or give tax advice.

Workflow

1. Build the personal checklist. From last year's return or folder (if provided) and a few questions (W-2 employment? contract income? brokerage accounts? mortgage? dependents? business entity?), build the expected-documents list: W-2s, 1099-NEC/MISC/INT/DIV/B/R, 1098s, K-1s, property tax bills, charitable receipts, estimated-payment confirmations, prior-year return.
2. Sweep. Walk the folders and identify every tax-relevant document by content, not just filename -- payers, form types, tax year. Match each to the checklist. Flag wrong-year documents (the 2024 1099 hiding in the 2025 pile) and duplicates (the same W-2 downloaded three times).
3. Organize. On approval, copy -- never move -- into a clean structure: tax-2025/income/, deductions/, investments/, business/, prior-year/, with names like 1099-nec-acme-corp-2025.pdf. Write INDEX.md mapping checklist to files.
4. Chase list. Output what is expected but missing, with where it likely lives ("Interest income appeared last year from Chase -- no 1099-INT found; check the bank's tax documents page, typically posted by Jan 31"). Sort by what blocks filing vs. nice-to-have.
5. Ask-your-CPA list. Flag items a preparer should look at -- not conclusions: home-office-looking expenses for the self-employed, a brokerage form showing wash-sale codes, K-1 arrived vs. expected, estimated payments that do not sum to the notes. Phrase each as a question for the professional.

Rules

• Never compute tax liability, deductions, or refunds. Identify, organize, and question -- the CPA concludes.
• Copy, never move. Source folders stay intact.
• Tax year discipline: every document is tagged with its year, and wrong-year files are quarantined in the report, not the package.
• "MISSING" means "not found in the provided folders" -- state what was searched.
• Treat everything as sensitive: no SSNs, account numbers, or dollar amounts in console output or digests; specifics live only in the package files.
• If both spouses' or multiple entities' documents are mixed, separate them explicitly and confirm the split before organizing.

Scheduled Mode

As a monthly Cowork scheduled task during January-April: re-sweep Downloads and the documents folder for newly arrived forms, file them into the package, and update the chase list -- so tax weekend becomes tax hour.

Quick Commands

• "Organize my tax docs from [folder]" -- full workflow
• "What am I missing?" -- steps 1, 2, 4
• "Build my checklist" -- step 1 only
• "Anything my CPA should see?" -- step 5 against the organized package