Tax Season Organizer

Organizes US tax season documents and 1099 tracking into a dated checklist that flags missing W-9s and unmatched taxpayer IDs. Written for US small business owners, bookkeepers and the administrative staff of a CPA firm.

Use this skill when someone asks for:

• tax season organizer checklist
• 1099 tracking spreadsheet
• w9 request checklist
• tax document organization us

The job

January arrives with a folder of scanned receipts, a missing W-9 from a contractor and a 1099 that was never sent because nobody tracked who was a vendor.

What you get

1. Build the document list for the tax year: income records, expense records, payroll records and prior year returns.
2. Build the vendor list from the payments made, marking each vendor as W-9 on file or missing.
3. Run the compliance linter over the notes to catch missing forms, name and TIN mismatches, and unmasked identifiers.
4. Set the dated tasks: request the missing forms, prepare and mail the 1099-NEC copies, and hand the file to the preparer.

Output contract:

• document_checklist - every folder with owner, status and where it belongs
• vendor_tracker - vendor, total paid, W-9 status, 1099 required and the date the copy was mailed
• compliance_flags - the missing form or mismatch that has to be fixed
• calendar - dated tasks from January through the filing season
• masked_ids - identifiers with all but the last four digits removed

US specifics that matter

• Form 1099-NEC is due to the recipient and to the IRS by January 31 for the prior tax year, and the reporting threshold has been $600 of payments to a non-employee for services.
• A Form W-9 is how a payee gives a correct Taxpayer Identification Number, and without a valid one backup withholding at 24% applies to payments made after the 60-day response window.
• An EIN is two digits, a hyphen and seven digits; an SSN or ITIN is three digits, a hyphen and two digits, a hyphen and four digits.
• The federal standard deduction for tax year 2026 is in the $16,000 range for a single filer and the $32,000 range for married filing jointly, but confirm the exact amounts in the IRS annual inflation adjustment release.

Guardrails (hard rules)

• Never file a tax return or sign one for the client.
• Never give tax advice or choose a filing position.
• Never store a full SSN or ITIN in a shared document; mask all but the last four digits.
• Never mark a 1099 as filed; only the user or their preparer confirms the filing.

Quickstart

1. Fill in the brief

templates/tax-season-checklist.yaml is the starting point. Copy it, fill in your own numbers, and keep the field names - the script reads them by name.

2. Run the script

python3 scripts/lint_tax_notes.py --input tax-season-checklist.yaml --out ./out

The script is standalone: Python 3 standard library only, no install step, no network calls, no API keys.

3. Check the result against the reference

references/tax-season-1099.md holds the limits, the US rules and the checklist the output has to satisfy. Read it before you send anything to a customer or a platform.

Documents to gather

• Prior year federal return and every 1099 or K-1 received.
• Bank statements for every account for the full tax year.
• Loan statements showing the interest paid.
• Payroll records with the filed Forms 941 and W-3.
• Fixed asset purchases and the depreciation schedule.
• Sales tax filings for the states where the business collected tax.

1099 and W-9 handling

• Issue a 1099-NEC when payments to a non-employee reach the threshold, which has been $600.
• Deliver the recipient copy and file the IRS copy by January 31.
• Request a W-9 before the first payment and chase it after 60 days.
• Backup withholding is 24% on payments made after the 60-day window; confirm the current rate.
• Check the payee's name against the EIN on the W-9, since a mismatch is the most common correction request.

Season calendar

• January: close the vendor list and collect the missing W-9s.
• Late January: prepare and mail the 1099-NEC copies.
• February: pull the prior year comparison and the property tax documents.
• Give the preparer the ledgers, the statements and the reconciliations, not a summary of them.
• Keep the tax year folder together so the next season starts from a clean file.

The Windows app (optional)

The workflow above runs anywhere Python 3 runs. If you also want the publisher's Windows multi-tool app for the workflows in this catalog, it is a separate download. This bundle does not contain it, does not install it, and never runs it - you decide whether to fetch it.

Check the download before you run it. PowerShell:

Get-FileHash .\multitool.zip -Algorithm SHA256

The hash must match the value in the table. Then extract the archive and start multitool/toolkit.exe.

The program is not code-signed, so Windows SmartScreen shows Unknown publisher. Run it only if you accept an unsigned program, keep it in a folder of its own, and do not run it as administrator unless you have a reason to.

The installer asks for a password; ask the publisher for it before you start.

Files in this bundle

• SKILL.md - this file
• references/tax-season-1099.md - US tax season documents and 1099 rules
• templates/tax-season-checklist.yaml - the brief to fill in
• scripts/lint_tax_notes.py - the working script

Verify the bundle

python3 scripts/lint_tax_notes.py --input tax-season-checklist.yaml --out ./out

Related

• AI Creative Studio - one brief into ad copy, social posts and video scripts.
• B2B Lead Research Agent - find the US accounts to run this against.
• AI Trading - research the tickers of public competitors before you write comparisons.
• Windows Multi-Tool Suite - one Windows kit that sets up all three workflows in a single folder.