It might feel like we just packed away the holiday decorations, but for landlords, January isn’t just about New Year’s resolutions—it’s the unofficial start of tax season prep. The April 15th deadline always sneaks up faster than expected, and the last thing you want is to be scrambling for receipts and statements in the spring.

As a landlord myself, I can tell you this: organization is everything when it comes to taxes. The better prepared you are now, the smoother your filing process will be (and the less painful those CPA invoices will feel). Here’s a breakdown of what you should start gathering right away.

1. Income Records

The IRS is going to want to know how much rental income you collected in 2025. That means:

• Rent payments (including late fees or pet fees)
  

• Parking, storage, or laundry income
  

• Any other miscellaneous payments from tenants
  

If you’re using property management software, a lot of this can be pulled in one report. If not, now’s the time to reconcile your bank deposits with what tenants paid.

2. Expense Documentation

Every dollar you spend running your rental is a potential deduction—if you’ve got the paperwork to back it up. Start gathering receipts and invoices for things like:

• Repairs and maintenance (plumbing, electrical, HVAC, etc.)
  

• Property management fees
  

• Insurance premiums
  

• Utilities (if you cover them)
  

• Advertising costs for vacant units
  

• Professional services (legal, accounting, bookkeeping)
  

A good rule of thumb: if you spent money to keep your rental business operating, save the documentation.

3. Mortgage Interest and Loan Documents

Your lender should send you Form 1098 in January showing the interest you paid in 2025. This is usually one of the largest deductions landlords get, so make sure it’s front and center. If you refinanced, hold onto those closing documents too—some costs may be deductible over time.

4. Property Tax Records

Don’t forget your city or town property tax bills. Those payments are deductible and can add up quickly, especially if you’re holding multiple units.

5. Depreciation Schedules

If you already own rental property, your CPA should have you on a depreciation schedule. Make sure you have the latest version ready to go. If you bought new property in 2025, your accountant will need your closing statement (HUD-1/ALTA) to set up depreciation properly.

6. Mileage & Travel Logs

Do you drive to your properties for inspections, maintenance, or tenant meetings? The IRS lets you deduct mileage or actual expenses. But—and this is key—you need to keep records. Whether it’s a mileage tracking app or an old-school logbook, start pulling that information together now.

7. 1099s for Contractors and Vendors

If you paid any contractor or vendor more than $600 in 2025, you may need to issue them a 1099-NEC. The deadline for sending these out is January 31, 2026, so don’t wait until April to deal with it.

8. Organize Digitally

One of the best moves you can make is going paperless. Scan receipts, invoices, and closing documents into digital folders labeled by property and year. Not only does this make life easier during tax season, but if you’re ever audited, you’ll look like a rockstar.

Final Thoughts

The difference between a stressful tax season and a smooth one usually comes down to organization and preparation. If you take time now, in January, to gather these documents, April won’t feel nearly as overwhelming.

At Ironclad, we see owners every year who wait until the last minute and end up missing out on deductions—or worse, paying penalties. Don’t let that be you.

Disclaimer: I’m not a CPA or tax advisor. This blog is for educational purposes only. Always consult with a qualified tax professional about your specific situation.