Bookkeeping, hands down. Thankfully, I found a competent, local guy who's genuinely affordable and capable. He even offered to help build out the bookkeeping portion of my real estate operations platform.
Maintenance coordination is assessing and assigning the right vendor for the job. If you have property accessibility for contractors you trust then it's relatively simple to handle maintenance requests. I know most owner operators have a hard time letting go of handling requests themselves - mostly to save money. But after a while, it becomes a burden - although my father genuinely loves handling maintenance requests and interacting with the tenants. To each is own!
Appreciate the honesty, Joseph. Props to your guy for building out your whole operations platform. That's next-level.
Totally agree on maintenance too. It's one of those things that feels simple until you're juggling 5 vendors at once.
If you ever come across a small landlord (up to 10 doors) who's drowning in receipts or chasing rent, I'd appreciate the intro. I specialize in clean books for long-term rentals. Just happy to help if the fit's right.
Outsource the task that eats your week but carries the least judgment first. For most self-managers that is maintenance dispatch and showings, not decisions about tenants or money. I keep renewals, rent collection decisions, and bookkeeping in house because those are where the relationship and the numbers live. When you hire help, write down the scope before the first job: response time, who approves spending above a set amount, and how you get photos and invoices. Pay for a small trial job before you hand over a whole process. The expensive mistake is hiring someone to save time, then spending that saved time checking their work because nothing was written down.
For me, it's receipts and categorization. I've seen too many owners lose hours matching bank entries to invoices at tax time. Clean books aren't glamorous, but they're the one thing I'd hand off before anything else.