tax-prep

tax-season-organizer

• --mode

  (default: infer from date — Q1-Q3 defaults to

  quarterly

  , Q4/Jan defaults to

  both

  ) —

  quarterly

  for estimated tax payment,

  1099

  for year-end 1099-NEC prep,

  both

  for combined

• --year

  (default: current year)

Step 1 — Determine mode

--mode

1. Check the current date. If Oct–Jan, default to

   both

   . Otherwise default to

   quarterly

   .
2. Confirm with the owner: "Based on the time of year, I'll prepare [mode]. Want me to do something different?"

Step 2 — Quarterly estimated tax (if mode includes quarterly)

1. Pull YTD Profit & Loss from QuickBooks (Jan 1 through last completed quarter).
2. If QuickBooks is not connected, ask the user to paste net income or upload a CSV.
3. Ask: "How much have you already paid in estimated taxes this year?"
4. Calculate: SE tax, adjusted net income, federal income tax estimate (default 22% bracket), quarterly payment due.
5. State every assumption explicitly — bracket, business type, exclusions.
6. Deliver the formatted estimate with the due date for the current quarter.

Step 3 — Year-end 1099 prep (if mode includes 1099)

1. Pull contractor/vendor payments from all connected sources: QuickBooks, PayPal, Stripe.
2. Aggregate by payee across sources. Flag likely duplicates for human review — never auto-merge.
3. Apply the $600 threshold. Flag near-threshold payees ($400–$599).
4. Check W-9 status in QuickBooks for each flagged payee.
5. Deliver the 1099-NEC candidate list with missing W-9 action items and the PayPal/Stripe 1099-K overlap note.

Approval gates

• Not tax advice. State this in every output header.
• State every assumption. Bracket, business type, excluded deductions — give the accountant the levers.
• Don't merge payees automatically. Flag duplicates for human review.
• Don't file anything. Output is prep material only.

Output