Seasonal Maintenance for Your Rental Portfolio (and Your Books!)

As a real estate investor, you already know that rental properties need seasonal checkups—clean gutters, serviced HVACs, and a good once-over before weather shifts. But what about your books?

Just like your properties, your finances benefit from regular maintenance. Waiting until tax season (or a major problem) to do a full review is like skipping oil changes and hoping the engine runs fine forever.

Here’s how to keep both your rentals and your records running smoothly—season by season.

🌷 Spring: Refresh & Review

For Your Properties:

• Inspect roofs and gutters after winter

• Schedule HVAC servicing before the summer heat

• Refresh landscaping and curb appeal

For Your Books:

• Reconcile Q1 bank accounts and credit cards

• Review income and expenses by property—anything off?

• Update your chart of accounts if something isn’t working

• Clean up any uncategorized transactions

Bonus: Review your insurance policies—spring is a good time to shop rates or increase coverage if values have gone up.

☀️ Summer: Optimize & Streamline

For Your Properties:

• Knock out big exterior projects while the weather’s good

• Check for pest issues and water damage

• Schedule mid-lease inspections if applicable

For Your Books:

• Automate recurring expenses (utilities, mortgage payments, software)

• Organize digital receipts from the first half of the year

• Set a mid-year meeting with your CPA or bookkeeper

• Prep estimated taxes if needed

Tip: Summer is a great time to revisit your goals and budget. Are you on track for what you projected in January?

🍂 Fall: Prep for What’s Ahead

For Your Properties:

• Winterize irrigation and inspect plumbing

• Trim trees and clean up the yard

• Replace air filters and test smoke detectors

For Your Books:

• Start collecting vendor W-9s for 1099s (don’t wait!)

• Review all maintenance expenses—are any creeping up?

• Identify deductible expenses you still need to capture

Bonus: Now’s the time to make big purchases if you’re planning on writing them off before year-end.

❄️ Winter: Wrap Up & Reflect

For Your Properties:

• Check for drafts and heat loss

• Monitor pipes during freezes

• Stay in touch with tenants over holiday travel plans

For Your Books:

• Do a full year-end reconciliation

• Review P&Ls by property and overall

• Close out open invoices or unpaid vendor bills

• Back up your bookkeeping data

And most importantly: Use the quiet season to reflect on wins, losses, and lessons from the year. Clean books make this easy to do—dirty books make it almost impossible.

Final Thought

Keeping your rentals in good condition protects your investment. Keeping your books in good condition reveals how that investment is really performing.

Build both into your seasonal routines and you’ll make smarter, faster decisions year-round—with fewer surprises come tax time.

Need help building a bookkeeping system that keeps up with your portfolio? That’s what I do. Let’s get your financial maintenance plan in place before next season rolls around.