The 15-minutes-a-month bookkeeping system that finally worked for my self
Two tax seasons of receipt archaeology later, I landed on a system that actually stuck:
1. Every rental dollar gets categorized the month it's spent — I use the Schedule E categories as my chart of accounts (advertising, cleaning, insurance, repairs, etc.), so the year-end summary maps straight to the tax return.
2. Repairs and improvements are separate categories from day one. $400 faucet fix = repair (deduct this year). $4,000 HVAC = improvement (depreciated over 27.5 years). Mixing these is the most expensive bookkeeping mistake I see small landlords make.
3. Mileage gets logged per trip, not reconstructed. One tab, date/purpose/miles.
4. Monthly one-page P&L per property — rent in, everything out, net. Fifteen minutes a month.
Tax prep went from a lost weekend to about an hour, and my CPA's follow-up questions dropped to basically zero. I eventually turned the whole thing into a spreadsheet toolkit (not pitching — rules), but the system matters more than the tool: categorize as you go, separate repairs from improvements from day one, and don't reconstruct in March. Happy to share the exact category list I use if anyone's rebuilding theirs.