Tax Season Organizer

Framing: This skill produces prep material for a CPA, not tax advice. Say so early and state every assumption explicitly so the accountant can adjust.

Quick start

Determine which mode the user needs, pull the relevant data, calculate or compile, and deliver a structured document the accountant can work from directly.

User: "what do I owe for estimated taxes this quarter?"
→ Pull YTD P&L from QuickBooks
→ Calculate estimated federal income tax + SE tax
→ Subtract payments already made this year
→ Show Q-specific amount due with due date and assumptions stated
→ Output: "Estimated Q2 payment due June 16: $X — see full breakdown below"

User: "I need to send out 1099s"
→ Pull all contractor/vendor payments from QuickBooks + PayPal + Stripe
→ Identify contractors paid ≥ $600 YTD
→ Flag records missing W-9 / EIN
→ Output: 1099-NEC candidate list + missing W-9 action list

Determine mode

Read the user's message and context to decide which path applies:

• Quarterly estimate — keywords: estimated payment, quarterly taxes, how much to set aside, safe harbor, Q1/Q2/Q3/Q4
• Year-end 1099 prep — keywords: 1099, 1099-NEC, year-end, contractors, W-9, send 1099s, file 1099s
• Combined — some users will ask "year-end summary" and need both. Run quarterly last; run 1099 prep first since it drives the most action items.

If the intent is ambiguous, ask: "Are you looking at your estimated tax payment for this quarter, or are you preparing 1099s for your contractors — or both?"

Path 1: Quarterly estimated tax

1. Pull YTD financials

Use QuickBooks to pull a Profit & Loss report from January 1 of the current year through the last day of the most recently completed quarter. Capture:

• Gross revenue (total income)
• Total expenses (operating expenses, COGS, etc.)
• Net ordinary income = revenue − expenses

If QuickBooks is not connected, ask the user to upload a P&L as CSV or paste the key numbers. For field names and query approach, see reference/connector-queries.md.

2. Ask about prior estimated payments

Before calculating, ask: "How much have you already paid in estimated taxes so far this year?" If the user doesn't know, note that you'll calculate total liability — they can subtract payments themselves or check with their accountant.

3. Calculate estimated liability

See reference/calculation-assumptions.md for the full math and the assumptions table you must include in output.

Short version:

1. SE tax = net profit × 0.9235 × 0.153 (then halve it — the deductible half offsets income)
2. Adjusted net = net profit − (SE tax / 2)
3. Federal income tax = apply the bracket rate appropriate to the user's business type and estimated annual income (default to 22% unless the user tells you their bracket; note this assumption explicitly)
4. Total annual liability = federal income tax + SE tax
5. Quarterly payment = (total annual liability − payments made) ÷ quarters remaining
6. Safe harbor check — note whether the user should verify against prior-year tax (100% of prior year, or 110% if AGI > $150k)

4. State assumptions and deliver output

Use this output structure:

Structure the output as a document with these sections in order:

1. Header — H2 with "Estimated tax summary" followed by the quarter and year. Subline: prepared date and "For review by your accountant."

2. YTD snapshot — Bold lines showing YTD net profit with date range, estimated annual net profit (annualized from YTD), and assumed business type (sole proprietor, S-corp, etc. — flag as assumed, not confirmed).

3. Self-employment tax — Show the SE tax calculation: net profit times 92.35% times 15.3%, and the deductible SE half.

4. Federal income tax estimate — Adjusted net income, assumed bracket

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