Three November Moves That Make Tax Season Easier

By Evan Garber, CFO and real estate investor for 20 years

I started my career as a CPA, then became an accounting-tech entrepreneur and CFO, and I sometimes still have trouble motivating myself to put my own books together. More than once I’ve put off updating my books until December, then spent a painful weekend catching up and telling myself that next year would be different. Much of the time goes to chasing down silly things like bank statements, receipts for capitalized items, and expenses paid personally that are for one of my properties.

Maybe you have a bank feed with an AI agent categorizing everything for you. You may not be done quite yet. While it can categorize a Home Depot charge, only you know whether that charge bought a repair or a capitalized asset, and for which property. Here are three things to do in November so your December weekends stay accounting-free.

1. Review and verify your books, then hand your CPA a complete package

Before anything goes to your CPA, run three checks on the books themselves:

• Reconcile every bank, card and loan account through October, then monthly. Most accounting systems do this fairly efficiently.
• Review categories by vendor rather than by transaction. Check property management fees, repairs against improvements, mortgage principal, and tenant deposits. One bad rule repeats its error all year. A common one is the full mortgage payment landing on the income statement, when only the interest belongs there. The principal reduces your loan balance.
• Verify that every transaction carries its property and entity, and that you’ve removed any personal spending and added any property expenses you paid personally.

Whoever keeps your books and prepares your return works from what you give them. A complete package in December, rather than pieces trickling in through March, means less of their time spent starting and stopping on your financial data, and a return that can be finished sooner. Start it now and add the year-end forms as they arrive in January. For each entity:

• Bank, credit card, loan and reserve account statements through December 31, or read-only access.
• Year-end owner statements from your property manager, plus any 1099s they issue to you.
• What you paid directly, since property manager statements generally leave it out: mortgage, insurance and property taxes, with the mortgage interest statement (Form 1098) when it arrives.
• Closing statements for anything you bought, sold or refinanced.
• A list of capital improvements by property, such as a roof, an HVAC system or a major remodel, with the invoices and the dates the work was finished.
• Contractor W-9s and what you paid each one.
• A list of security deposits held, by tenant.
• A short note on anything new or unusual: a new LLC, a property placed in service, a long vacancy, or personal use.

2. Collect W-9s now for 1099 season

The good news for 2026: for most contractor and rent payments made in 2026, the 1099 reporting threshold is $2,000, up from $600, and may be adjusted for inflation beginning with 2027 payments.

W-9s are easiest to collect in November, and the IRS can charge a penalty for each late or incorrect 1099, plus interest. Pair each W-9 with the year’s total paid to that contractor, since the threshold applies per payee. Gather them now, by entity, ahead of these dates:

• 1099-NEC: due Monday, February 1, 2027 (January 31 is a Sunday).
• 1099-MISC (rents and similar payments): due to recipients February 1, 2027.
• Card and payment-app payments go on Form 1099-K instead, which the card company or app files.

Payments to businesses taxed as corporations, including LLCs that elected corporate treatment, generally need no 1099, except for medical or legal services. The W-9 shows how each contractor is taxed. If your property manager pays vendors from your funds, ask which forms it files for you, and check with your CPA whether these rules apply to your rental activity.

3. Review your move-out process for Colorado’s deposit changes

Colorado changed its security deposit law on January 1, 2026.¹ The new rules tighten what counts as normal wear and tear, put a documentation requirement behind every deduction, and raise the cost of getting it wrong. Five areas deserve a fresh look:

• Timing. The default window to return a deposit is now 30 days, and a lease can extend it up to a cap. Confirm your lease and your calendar reflect that.
• Written reasons. Every deduction needs a written statement of the specific reasons. Build the exact reasons and amounts into your template.
• Documentation. Keep photos, inspection reports, receipts and estimates for every move-out. Tenants can request them, and the burden of showing a deduction was justified falls on you.
• Wear and tear. The legal definition got broader, so compare it to your standard deduction list.
• Consequences. Missing a requirement can cost you the right to keep any of the deposit, and wrongful withholding can bring treble damages.

If you are selling a property, the deposits have to move to the buyer or go back to the tenants within a set window, so build that into your closing checklist. Have your attorney review your lease and move-out process before your next turnover.

On the books, a deposit you plan to return is a liability, and IRS guidance says to leave it out of income when received.²

In Summary

None of this grows your portfolio, but most of it is easier to address in November than in March.

Questions about any of this? Reach me at evan@balancedlive.ai.

Additional Resources

BalancedLive. Evan built BalancedLive because generic accounting software never fit how investors hold property. It keeps the books for every property and entity in one place. Transactions get matched, categorized and routed to the right entity and property, and anything unclear gets flagged for your review before month end. Your bookkeeper and CPA can log in with their own access, and one dashboard shows value, equity, loan to value and net operating income across your whole portfolio.

Visit BalancedLive to see how it works or request a demo.

Learn more about Evan and BalancedLive on his Colorado RE•CON partner page.

Notes

1. Colorado HB25-1249; C.R.S. 38-12-103.
2. IRS Publication 527, Residential Rental Property.

This article is general education, not tax or legal advice. Consult your CPA or attorney about your situation.

About the Author

Evan Garber is a former CPA, tech founder, CFO, and Colorado real estate investor of 20 years. He co-founded a tech startup in the ERP space and led it for 22 years. Generic accounting software never fit how investors operate, so he recently founded BalancedLive: a complete portfolio accounting solution for real estate investors and their bookkeepers.

Email: evan@balancedlive.ai
LinkedIn: Evan Garber