Summer Tax Prep: Why Now Is the Time to Get Ahead

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Episode Summary

February is too late for tax prep. By the time most landlords think about taxes, the tax year is already locked — and whatever deductions they missed, whatever decisions they wish they’d made differently, that window has closed.

In this episode, we make the case for why summer is actually the most strategic time of year to get your rental finances in order. With several months still left in the tax year, there’s still time to track expenses, run a mid-year financial check-in, clean up your records, and have a real planning conversation with your CPA before year-end — not a post-mortem one in January.

We also share a personal story about missing a significant expense on one of their own properties — and why by the time they caught it, it was too late to do anything about it.

What You’ll Learn in This Episode

• Why summer — not January — is the best time to focus on your rental finances
• The three things every landlord should be doing right now to get ahead on taxes
• How to do a mid-year financial check on your rental property (and what questions to ask)
• Why clean books in the fall means a strategy conversation with your CPA instead of an expensive cleanup
• How accounting tools like QuickBooks, TurboTenant, DoorLoop, RentRedi, and Innago can make this easier
• Why QuickBooks works great for some landlords — and why it’s not the right fit for everyone

Key Takeaways

1. Get Your Expense Tracking Current — While It’s Still Fresh

Summer is when most of your maintenance and repair expenses are happening: HVAC servicing, painting, fence repairs, appliance replacements. If you’re not logging those expenses as they happen, you could be sitting on deductions you don’t even know you have. Legitimate rental expenses are generally deductible in the year you pay them — but only if you track them.

Stacie and Kevin share a personal example of missing a couple-thousand-dollar deduction because an expense was charged to a personal credit card and never logged against the property. By the time they found it, amending the return wasn’t worth the cost.

2. Run a Mid-Year Financial Check on Every Property

Getting your expenses current is just the start. The real value is pulling an actual profit and loss number — money in, money out, by property — so you can make informed decisions before December instead of discovering problems in February when most people do their tax prep.

Questions to ask yourself mid-year:

• Are you holding adequate cash reserves? (Rule of thumb: 10–15% of gross rents)
• Are all security deposits held separately and in the correct amounts?
• When does your insurance renew — and is your coverage still adequate?
• Are your property taxes assessed correctly? (If values have fallen, reassessment may save money)
• Who pays utilities? Is there room to add fees or recapture expenses?
• What planned maintenance or improvements could be completed before year-end to be deducted this tax year?

3. Build Clean Records Before Your CPA Conversation

If you walk into a fall planning meeting with messy books, your accountant spends their time — and your money — on data entry instead of strategy. If you walk in with clean, current financials, that conversation can actually be about decisions.

QuickBooks Online allows you to invite your CPA directly as an Accountant user, giving them full view-and-edit access to your books. Many CPA firms already use QuickBooks, which means a clean QuickBooks file can eliminate a significant amount of manual data transfer at tax time.

Accounting Tools Mentioned in This Episode

We use QuickBooks to invoice tenants and auto-code income directly to the right accounts — no manual entry, no end-of-month reconciling. However, we’re clear that QuickBooks works well for us specifically because Stacie has an accounting and finance background. For landlords without that background, the setup learning curve is real.

Property management platforms that build accounting directly into their products — like TurboTenant, DoorLoop, RentRedi, and Innago — may be a better fit for landlords who want Schedule E categories and income/expense tracking built in from day one. DoorLoop and RentRedi also offer QuickBooks sync for landlords who want both systems working together.

Affiliate Disclosure: This episode contains affiliate links. Your Landlord Resource may earn a commission if you purchase through our links, at no additional cost to you. We only recommend products and services we believe in.

Legal Disclaimer: Nothing in this episode constitutes personalized tax, legal, or financial advice. Always consult a licensed CPA or real estate attorney for guidance specific to your situation.

Links & References Mentioned in This Episode

Episode 12: Our Experience With a 1031 Exchange, Would We Do It Again?

Episode 18: 7 Ways to Increase Profit for Your Rental Property

Episode 28: The Cash Reserves Blueprint: Protecting & Expanding Your Portfolio

Episode 45: Basic Tax Strategies For Real Estate Investors

Episode 46: Advanced Tax Strategies for Your Real Estate Portfolio

Episode 55: Preventative Maintenance That Brings Peace of Mind

Episode 79: Accounting Software Options for Real Estate Investors

Episode 99: 5 Oversights That Drain Your Income

Episode 111: Stop Guessing, Start Budgeting

Good Read: Basic Tax Strategies 

Good Read: Advanced Tax Strategies Book    

QuickBooks (30% off first 6 months):

TurboTenant Create a FREE account today!

DoorLoop: Syncs Directly to QuickBooks

RentRedi: Syncs Directly to QuickBooks

Innago: Create a FREE account today!

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Estimated reading time: 3 minutes