Working on a Bookkeeping AI Agent For My Rentals

[Andrew Ferguson]

I'm working on an AI bookkeeping agent to help with some of my bookkeeping tasks. I started this because I found myself asking a chatbot to turn some of my PDFs into quickbooks upload-able CSVs. Like me I'm sure many people have asked a chatbot how to do a particular accounting thing as well. I started looking into more things a LLM (large language model) would be capable of doing and started working on a couple features to help with some of the repetitive data entry I was doing every month.

I'm curious about learning how people do bookkeeping and some of the things they dread doing? What do others do for bookkeeping? Even professional bookkeepers, what tasks are tedious and you wish could be automated?

[Jason Malabute]

AI can absolutely assist with bookkeeping, and tools like QuickBooks have been using AI-driven transaction categorization for years. That said, based on my experience working with real estate bookkeeping clients and using AI tools internally, AI still has meaningful limitations.

AI is good at recognizing patterns, but bookkeeping—especially for real estate—is full of nuance: distinguishing repairs vs. improvements, properly handling owner contributions and distributions, allocating expenses across properties, class tracking, loan activity, depreciation-related items, and state-specific considerations. These are areas where AI often struggles or makes assumptions that look reasonable but are technically incorrect.

Because of that, AI still requires strong human oversight. Someone knowledgeable has to review, correct, and contextualize what the system is doing to ensure the books are actually accurate and tax-ready.

I’d also caution against fully “hands-off” AI bookkeeping solutions. There was a company last year that attempted to automate bookkeeping entirely with AI, and it ultimately failed—largely because accuracy and accountability broke down without proper human review.

In my view, AI is best used as an efficiency tool to reduce repetitive work, not as a replacement for experienced bookkeeping judgment—especially in real estate.