Year-End Landlord Tax Prep Checklist: What to Gather Before You Meet Your Preparer

Tax prep for a rental shouldn’t start in March. Spread the work across December, January and February and it shrinks to a few short sessions: reconcile, collect, summarize, hand off. This checklist is organized by month and ends with the single folder your preparer actually needs.

December: close the year cleanly

Reconcile the books

• Every rental bank and card transaction for the year is categorized by property and Schedule E line
• Each account’s year-end book balance matches the December statement
• Rent received per unit matches your rent roll. Note any unpaid balances (unpaid rent generally isn’t income for cash-basis landlords until it’s received)
• Personal transactions that slipped into rental accounts are marked as such
• Platform payouts are recorded at gross rent with fees separate. See collecting rent online

If you use Stessa, its Schedule E report is on the Manage plan and up. On the free plan you can export transactions. Baselane lists Schedule E reports among its features. With a spreadsheet, check that your category column maps every expense to one line. Whatever the tool, export a full-year transaction CSV and save it to your records folder.

Tidy up the paper trail

• Receipts exist (and are named consistently) for expenses above your threshold. See organizing rental records
• Large purchases are flagged as possible improvements with invoice, date placed in service and description
• The mileage log is complete, with totals split by rate period (2026: 72.5¢ Jan–Jun, 76¢ Jul–Dec). See mileage tracking
• Odometer reading recorded on December 31

Contractors and 1099 prep

• List every individual or unincorporated business you paid for services on the rental, with annual totals
• Confirm you have a Form W-9 for each. Request any missing ones now, while people still answer
• Note how each was paid. Payments by credit card or through payment apps are generally reported by the payment processor on Form 1099-K, not by you
• Ask your preparer whether your rental activity requires you to file 1099-NEC forms. For payments made in 2026, the IRS 1099-NEC reporting threshold is $2,000 (it was $600 for earlier years); see the IRS page Am I required to file a Form 1099?

Planning items to raise before Dec 31

• Large repairs or purchases you’re deciding on, whose timing could matter. Ask your preparer before acting
• Whether your prior estimated tax payments are on track. The 4th-quarter 2026 estimated payment is due January 15, 2027 per the 2026 Form 1040-ES

January: collect the forms

• Send any required 1099-NEC forms to contractors and file with the IRS. These are generally due January 31 (the next business day if that falls on a weekend). Confirm the date for your filing year
• Create next year’s folders and roll your reserve and rent-roll trackers forward

February: build the preparer packet

Put everything into one folder per year, organized like this:

1. Per-property income and expense summary by Schedule E line

Leave line 18 (depreciation) to your preparer unless you maintain the schedule yourself.

2. Items that aren’t on lines 3–19 but your preparer needs

• Capital improvements: date placed in service, description, cost, invoice
• Mortgage principal paid (not deductible, but useful for reconciling the loan)
• Business miles per property, split by rate period, plus parking and tolls
• Fair rental days and personal use days per property (line 2)
• Security deposits held at year-end, and any amounts kept during the year. See deposit basics
• Purchases or sales of property this year: closing statements

3. Source documents

• Forms 1098, 1099-K, 1099-MISC received
• Property tax bills, insurance declarations, HOA statements
• Full-year transaction export (CSV) and bank statements
• Mileage log
• Contractor list with W-9s and copies of any 1099-NECs you filed
• Last year’s return and depreciation schedule (new preparer only)

Questions to bring to your preparer

1. Which of my flagged purchases are improvements, and should we use the de minimis or other safe harbor elections?
2. Do I need to file 1099-NECs for any contractors?
3. Is my rental loss (if any) limited this year, and what carries forward?
4. Are my estimated tax payments right for next year, given rental income?
5. Is there anything I should track differently next year?

The whole checklist on one screen

• Books reconciled to statements, every transaction categorized
• Full-year ledger exported and saved
• Receipts named and filed; improvements flagged
• Mileage log totaled by rate period; Dec 31 odometer recorded
• Contractor totals listed; W-9s on file
• 1099-NECs filed if required
• 1098, escrow statement, property tax, insurance and HOA docs collected
• 1099-K / 1099-MISC reconciled to rent
• Per-property Schedule E summary built
• Improvements, principal, miles, rental/personal days listed
• Questions written down
• Next year’s folders created

Optional but handy for the physical side: a 13-pocket accordion file per tax year and a label maker for the file box. Paper records then mirror your digital categories.