Hey everyone, I’m a landlord myself with 18 units, across 10 properties —and for years, tax season was a source of dread. I remember spending entire weekends crunching numbers, gathering receipts from random shoeboxes and backtracking through countless transactions in my bank account. By the time I had everything together, I always felt like I was rushing, and I’d inevitably forget something.
Eventually, I realized that if I kept waiting until tax time to organize my books, I would never escape the stress (and extra CPA fees). So I committed to tracking everything throughout the year. Here’s what helped me most:
- Quarterly Check-Ins: I spend an hour each quarter reviewing my rental income and categorizing any expenses right away. This habit alone changed the game for me—I no longer have a mountain of data entry in March. We have a VA so she does all the tagging and I ask her to export it from Baselane, into excel, then I review it and give comments.
- Going Digital: Scanning and storing my receipts in real time saves me from searching for that one $17 plumbing supply receipt. It’s crazy how quickly those small things add up. Most of our receipts are digital (email) so we just put it in drive and attach it to Baselane transactions as we go (weekly). It's part of the VAs job to do this every day.
- Smart Banking/Tools: Full disclosure, I work at Baselane, a banking and finance platform designed for landlords. One reason I joined is because I genuinely needed the exact solution Baselane offers: a banking account that automatically categorizes rental transactions, streamlined reporting, and easy exports. But even if you’re not using Baselane, any tool that integrates with your bank and helps automate categorization can drastically reduce year-end headaches. You can integrate Baselane with Quickbooks for example.
- CPA Handoff: Once I started keeping my records tidy in real time, handing things off to my CPA became pretty painless. Instead of 30+ emails back and forth, now I just send them a consolidated report or grant them access to review transactions. This year, 96% of my transactions are already tagged for 2024, so I expect to do about 1 hour of cleanup before I send to my CPA.
Don’t get me wrong—I’m still learning new ways to simplify tax prep every year. But for me, the biggest shift was developing a routine and using tools that let me see my rental finances at a glance.
Anyway, that’s my two cents. If anyone else has a favorite strategy or tool they use to keep tax prep under control, I’d love to hear it! Always happy to swap ideas and keep refining this process.
