Outsourcing two rentals' books turned into six weeks of my own labor

The whole reason I own two rentals instead of doing anything else with the money is that I don't want a second job. So when the spreadsheet started taking me a Sunday a month I went and found a bookkeeper on a freelance marketplace for $180 a month, which felt like a bargain.

Three months in I asked her for a report by property and she sent me one file with everything combined. I asked again and she said the way I'd sent the transactions didn't distinguish them. Which was true. I'd been sending her one bank export.

So I fired myself and hired somebody who does real estate specifically, at about three times the price. Her first email asked for my depreciation schedule. I didn't know what that was and said so. She said it's the record of what each property and each big improvement cost, and how much of that cost has been written off each year, and that her work has to tie to it or my accountant and my books will be telling two different stories.

My accountant had one. He'd had one the whole time. Nobody had ever asked him for it including me.

Then came six weeks that were more work than the Sunday a month I was trying to escape. Closing statements from both purchases, the 2022 furnace, a bunch of Home Depot receipts I had to go dig out of an email account. She sent a list every Monday and I hated the list.

It's month nine now. I spend about twenty minutes a month on this and I get a report per property on the ninth. The $180 version was cheaper than the spreadsheet and worth exactly what the spreadsheet was worth.