At what number of properties did your bookkeeping system completely break down?
Genuine question for people who've been doing this for a while. Most investors start with something simple like a spreadsheet or a basic QuickBooks setup and it works fine for the first one or two properties. At some point though, it doesn't work anymore. Not dramatically but it just quietly starts failing. Transactions get harder to categorize, and you're not sure which property an expense belongs to. The monthly numbers take longer to pull together, and by year end you're handing your CPA a mess of receipts and spreadsheets. For some people that happens at property 3, for others it could be until property 7 or 8. And for people running multiple LLCs, the breaking point usually comes earlier than they expected because the entity separation adds a layer that most basic tools were not built to handle. I'm curious where people hit that wall.... and more importantly, what you actually ending up changing. Did you hire a bookkeeper, switch tools, or just restructure how you categorize? And looking back, do you think you waited too long to fix it?
- Aaron Weikle
