I built and paid for a full bookkeeping setup eleven months before I owned anything

I wanted to be ready. That was the whole logic and it cost me about $1,900.

Eleven months ago I formed the LLC, opened the business checking, subscribed to accounting software on the annual plan, added a receipt capture app, added a property management app with an accounting module because I'd read that the two together were the proper stack, and put a bookkeeper on a $95 a month minimum retainer so I'd have someone who already knew my file when the first rental closed.

The first rental has not closed. Two deals died at inspection, one I lost on price, and I'm still looking.

So eleven months of subscriptions and retainer on an entity whose entire transaction history is the state filing fee, the registered agent, and the software charges themselves. My bookkeeper has been reconciling a bank account that receives nothing and spends money only on the tools used to reconcile it. She told me in month three I should pause her and I said no because I thought the relationship was worth keeping warm. That was $95 times eight after she'd already advised against it.

Worse, the chart of accounts I built with her assumed a plan I've since abandoned. I designed it for small multifamily across three entities. I'm now looking at single family in one entity, and about a third of those accounts are for things that don't exist. Rebuilding is not expensive, it's just an admission that the eleven months of readiness produced nothing usable.

What I'd do differently. Bank account and a spreadsheet until there's a closing statement. Software starts the month the first rent hits. The bookkeeper gets hired after there are twelve weeks of real transactions to look at, because a chart of accounts designed against actual activity beats one designed against a plan. And when the person you're paying tells you to stop paying them, stop paying them.