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Category: Pricing & Revenue
By: James Wu
Reply by Priya Nair:
I've tried a few and landed on **QuickBooks Self-Employed** ($15/month) for 2 properties, then upgraded to **QuickBooks Online Essentials** ($30/month) when I hit 4 properties. For STR specifically: 1. **QuickBooks Online** — Most popular choice. Links to your bank account, auto-categorizes transactions by property using "classes" or "locations." CPA reports are one-click. $30/month. 2. **Stessa** — Free! Specifically designed for rental property investors. Tracks income, expenses, and generates Schedule E-ready reports. The catch: it's more focused on long-term rentals, so STR-specific features are limited. 3. **REI Hub** — Built specifically for real estate investors including STR. $15/month per property. Better categorization for STR deductions than generic tools. 4. **Wave** — Free basic accounting. Good enough for 1-2 properties if you're budget-constrained. My recommendation for 2 properties: start with Stessa (free) or REI Hub ($30/month total). Move to QuickBooks when you scale to 3+ properties or want more advanced reporting. The most important thing: separate business and personal finances. Get a dedicated business bank account and credit card. Makes tax time 10x easier regardless of which software you use.
Reply by David Okafor:
Pro tip that saved me thousands: track EVERY expense, no matter how small. That $8 roll of paper towels? Deductible. The $12/month for your Airbnb messaging tool? Deductible. Gas to drive to the property? Deductible. I use QuickBooks + the QuickBooks mobile app. When I buy anything for the STR, I snap a photo of the receipt in the app and it auto-categorizes it. At year-end, my CPA had everything organized and found $4,200 in deductions I would have missed with a spreadsheet.