Nobody buys an STR because they love bookkeeping. But messy books cost real money — missed deductions, tax penalties, and no idea whether you're actually profitable. The good news: one property needs about 30 minutes a month, if you set it up right.
Open a dedicated bank account and card for the property. All rental income in, all expenses out, nothing personal touches it. This one move does 80% of your bookkeeping automatically — the statement IS the ledger.
Many jurisdictions charge lodging/occupancy tax, and platforms collect and remit in some places, partially in others, and not at all in the rest — especially for direct bookings. Verify exactly what's remitted for your address, register with your locality if required, and calendar the filing dates. This is the compliance item that bites self-managers most.
A categorized income/expense summary, closing statements if you bought or refinanced, capital improvement receipts, mileage log, and days of personal use. We're operators, not tax professionals — talk to your CPA, ideally one who knows short-term rentals, because STR-specific rules are genuinely different.
ACTION: If property money still mixes with personal money, open the dedicated account this week. Everything else builds on it.
Final lesson in 2 days: you've built the machine — now scale it, or hand it off from a position of strength.