# Tax Prep Checklist > Creates tax preparation checklists organized by entity type with document gathering and deadline tracking. Use when preparing for business tax filing season. - Skill: `reaperinvest/tax-prep-checklist` (Agent Skill) - Install (CLI): `npx skillmds@latest add reaperinvest/tax-prep-checklist` - Raw SKILL.md: https://api.skillmd.com/api/skills/reaperinvest/tax-prep-checklist/raw - Safety review: pending - Works with: Claude Code, Claude.ai, OpenAI Codex - Category: Coding & Dev Tools - Author: reaperinvest (https://skillmd.com/u/reaperinvest) - Updated: 2026-09-22 - Page: https://skillmd.com/skills/reaperinvest/tax-prep-checklist --- # Tax Prep Checklist ## When to Use This Skill Use this skill when you need to: - Organize documents and information for business tax filing - Create a comprehensive tax prep checklist customized to your entity type - Track tax deadlines and filing requirements - Prepare for a meeting with your accountant or tax preparer **DO NOT** use this skill for tax advice, tax return preparation, or legal tax strategy. This is a document organization and preparation tool only. Always consult a qualified tax professional. --- ## Core Principle TAX PREP IS A DOCUMENT-GATHERING EXERCISE — THE CHECKLIST ENSURES NOTHING IS MISSED SO YOUR ACCOUNTANT CAN DO THEIR JOB EFFICIENTLY AND YOU PAY ONLY WHAT YOU OWE. --- ## Phase 1: Business Profile ### Required Inputs | Input | What to Ask | Default | |-------|------------|---------| | **Entity type** | "What is your business entity? (sole prop, LLC, S-corp, C-corp, partnership)" | Sole proprietorship / Single-member LLC | | **Tax year** | "What tax year are you preparing for?" | Previous calendar year | | **Revenue range** | "Approximate annual revenue?" | Under $250K | | **Has employees** | "Do you have W-2 employees?" | No — contractors only | | **State(s)** | "Which state(s) do you operate in?" | Single state | | **Accountant** | "Do you have a CPA or tax preparer?" | Yes | **GATE: Do not proceed without entity type and tax year.** --- ## Phase 2: Document Checklist ### Universal Documents (All Entity Types) ``` ## Tax Prep Checklist: [Tax Year] ### Business Information - [ ] EIN (Employer Identification Number) - [ ] Business legal name and DBA - [ ] Business address - [ ] Date business started (if new) - [ ] Prior year tax return (for reference) ### Income Documentation - [ ] Total gross revenue for the year - [ ] 1099-NEC forms received (for contract work performed) - [ ] 1099-K forms (payment processor reports — PayPal, Stripe, etc.) - [ ] 1099-MISC forms received - [ ] Other income documentation (interest, investments, rental) - [ ] Monthly/annual revenue reports from bookkeeping system ### Expense Documentation - [ ] Bank statements (all business accounts, all 12 months) - [ ] Credit card statements (all business cards, all 12 months) - [ ] Categorized expense report from bookkeeping software - [ ] Receipts for purchases over $75 (or your accountant's threshold) - [ ] Vehicle mileage log (if claiming business mileage) - [ ] Home office measurements and total home square footage (if applicable) ``` ### Entity-Specific Documents **Sole Proprietorship / Single-Member LLC:** ``` - [ ] Schedule C categories prepared (income, COGS, expenses) - [ ] Estimated tax payment records (4 quarterly payments) - [ ] Self-employment tax calculation - [ ] Health insurance premium records (for SE health deduction) - [ ] Retirement contributions (SEP IRA, Solo 401k) ``` **S-Corp / LLC taxed as S-Corp:** ``` - [ ] Officer compensation (W-2 for yourself) - [ ] Shareholder distribution records - [ ] Payroll tax filings (Form 941 quarterly) - [ ] Form W-3 (annual wage summary) - [ ] Reasonable compensation documentation - [ ] Shareholder loan documentation (if applicable) ``` **Partnership / Multi-Member LLC:** ``` - [ ] Partnership agreement (for profit/loss allocation %) - [ ] Capital account records for each partner - [ ] Partner contribution and distribution records - [ ] Schedule K-1 preparation data ``` ### Contractor and Employee Documents ``` ### If You Paid Contractors - [ ] 1099-NEC forms issued to contractors paid $600+ - [ ] W-9 forms on file for all contractors - [ ] Contractor payment records ### If You Have Employees - [ ] W-2 forms issued to all employees - [ ] Payroll tax deposits (federal and state) - [ ] Form 940 (FUTA) - [ ] Form 941 (quarterly payroll tax returns) - [ ] State unemployment tax filings - [ ] Workers' compensation records ``` --- ## Phase 3: Deduction Maximizer ### Commonly Missed Deductions Checklist ``` ## Deductions to Review - [ ] Home office deduction (simplified: $5/sq ft up to 300 sq ft) - [ ] Business mileage (check current IRS rate) - [ ] Health insurance premiums (self-employed deduction) - [ ] Retirement contributions (SEP IRA, Solo 401k) - [ ] Business insurance premiums - [ ] Professional development and education - [ ] Software and subscriptions (monthly tools add up) - [ ] Phone and internet (business use percentage) - [ ] Business meals (50% deductible — must document who + business purpose) - [ ] Professional services (accountant, lawyer, coach fees) - [ ] Bank and merchant fees - [ ] Depreciation on equipment and assets - [ ] Business travel expenses - [ ] Startup costs (if first year — up to $5,000 immediately deductible) ``` --- ## Phase 4: Deadline Tracker and Delivery ### Key Deadlines ``` ## Tax Deadlines: [Tax Year] | Form | Entity Type | Deadline | Extension Deadline | |------|------------|----------|-------------------| | Schedule C (with 1040) | Sole Prop | April 15 | October 15 | | Form 1065 | Partnership | March 15 | September 15 | | Form 1120-S | S-Corp | March 15 | September 15 | | Form 1120 | C-Corp | April 15 | October 15 | | 1099-NEC (to contractors) | All | January 31 | No extension | | W-2 (to employees) | All | January 31 | No extension | ### Estimated Tax Payments (Next Year) | Quarter | Period | Due Date | |---------|--------|----------| | Q1 | Jan-Mar | April 15 | | Q2 | Apr-May | June 15 | | Q3 | Jun-Aug | September 15 | | Q4 | Sep-Dec | January 15 | ``` ### Accountant Prep Package Organize all documents into this structure for your tax preparer: ``` tax-prep-[YEAR]/ ├── income/ ├── expenses/ ├── contractor-docs/ ├── payroll/ (if applicable) ├── prior-year-return/ └── notes-and-questions.md ``` --- ## Example: Solopreneur with LLC ($85K Revenue) **Entity:** Single-member LLC (taxed as sole prop) **Key items:** Schedule C, quarterly estimated tax payments ($5,200 paid), home office ($1,500 deduction), mileage (4,200 business miles), SEP IRA contribution ($8,500), health insurance premiums ($6,000). **Missing:** No mileage log — recommend reconstructing from calendar entries. No W-9 for contractor paid $2,400 — under $600 threshold per contractor, 1099 not required. --- ## Anti-Patterns - **Treating this as tax advice** — this is a preparation and organization tool. Always defer to a qualified tax professional for tax strategy. - **Waiting until April** — start gathering documents in January. The earlier you start, the more deductions you will find. - **Mixing personal and business expenses** — only include business expenses. If accounts are mixed, separate them before handing off to your CPA. - **Ignoring estimated tax payments** — solopreneurs who skip quarterly payments face penalties. Track all four payments. - **Shoebox of receipts** — categorized digital records save your accountant time (and your bill). Organize before the handoff. --- ## Recovery - **No bookkeeping system:** Walk through bank and credit card statements month by month. Categorize expenses into Schedule C categories. Recommend setting up bookkeeping for next year. - **Missing receipts:** Most deductions under $75 do not require receipts — bank/credit card statements suffice. For larger purchases, check email for digital receipts. - **Missed quarterly estimated payments:** Calculate the underpayment penalty exposure and include extra funds in the final payment. Set up autopay for next year. - **First year in business:** Flag startup cost deductions, ensure proper entity formation docs are on file, and set up quarterly estimated payments going forward.