Working on a Bookkeeping AI Agent For My Rentals

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Working on a Bookkeeping AI Agent For My Rentals

Andrew Ferguson
Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes

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?

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Jason MalabuteBusiness Member
Accountant · Los Angeles, CA · Member since 2016 · 2k+ posts · 912 votes
9mo

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.

Malabute & Company CPAs527 Reviews
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  • Dillon KennistonBusiness Member
    Financial Advisor · Sinking Spring, PA · Member since 2016 · 28 posts · 22 votes
    9mo

    Sounds cool. How are you getting transactions into the system?

    1Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    9mo

    Hey Dillon, Quickbooks Online has an API.

    0Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    9mo

    @Dillon Kenniston I'm thinking about developing this into an app others can use. I kind of prefer just to have a system with its own ledger (it's cleaner and easier). I just know a lot of people use QB and it may be easier to acquire users if you're solving a QB problem and not asking to be their total accounting solution.

    So I'm just trying to learn the landscape of bookkeeping a bit more outside my own experience.

    0Reply
  • Dillon KennistonBusiness Member
    Financial Advisor · Sinking Spring, PA · Member since 2016 · 28 posts · 22 votes
    9mo

    Totally get it. I'm in PropTech but B2B. Transaction data is a PITA.

    If your platform is D2C and clients have a portal to auth into, definitely, QB's API could be a win. Alternatively, maybe build for QB's app store?

    0Reply
  • Jake BakerBusiness Member
    Flipper/Rehabber · San Diego, CA · Member since 2020 · 1k+ posts · 696 votes
    9mo

    @Andrew Ferguson

    We are a bookkeeping company for real estate investors, so I am constantly looking at software that could potentially disrupt. There are some good QBO alternatives, like Digits, for simple businesses like freelancers. Unfortunately, real estate is very balance-sheet-heavy, requires a fair amount of human touch, and will likely be that way for a while. AI receipt capture has come a long way, and AI reporting insights have improved quite a bit. 

    I use QuickBooks Online for my flipping business, rentals, and bookkeeping clients. QBO has every feature you need to run a business, great reporting features, and integrates with more software than anything else. Like it or love it, recent data puts their share at approximately ~62% of the overall accounting software market. They have money and are pouring it into their Intuit Assist (AI chatbot) and Agents.

    [email protected]
    BookkeepingRE - Bookkeeping for Real Estate & Service-Based Businesses52 Reviews
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    1Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    9mo

    @Jake Baker I'm sure you have amazing insights. I did find Digits in doing my due diligence and I like it. It has some great features that make it more enjoyable than QB. And I think you're right about RE being a more unique industry. I feel like all general purpose software can for sure handle RE bookkeeping. You just really have to understand how what you're doing in the UI impacts the P&L and Balance Sheet. And to do that you have to understand the ledger and some of the more abstract accounting concepts.

    But there is also the tediousness. Processing any bill or statement is a multi-step job that includes not just entering the data into QB in several places during the lifecycle of the transaction but also sending emails to the property manager, sometimes logging in to systems to download PDF's etc. That's also part of the problem that I'd like to tackle. 

    0Reply
  • Jason MalabuteBusiness Member
    Accountant · Los Angeles, CA · Member since 2016 · 2k+ posts · 912 votes
    9mo

    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.

    Malabute & Company CPAs527 Reviews
    WebsiteView Page
    4Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 13k+ posts · 9k+ votes
    9mo
    Quote from @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?


    Your best bet is to pursue DIY landlords, but your biggest challenge with them will be getting them to pay for services.

    Just look at many of the posts here on BP where these owners are always searching for FREE tools and complaining about anything they have to pay extra for. 

    Shoot, even many rental owners that hire PMCs constantly complain about costs. 

    In our office, we have a running joke that we could work for free, but owners would still complain about material costs and such:(

    So, how would you keep your cost-structure low?


    [email protected]248-209-6824
    Logical Property Management4.9465 Reviews
    WebsiteView Page
    1Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    8mo

     @Jason Malabute I think your point is a good one. It may make more sense to build tools that make professional bookkeepers more efficient. They can guide an automation tool like an agent and easily spot mistakes early. Their benefit would be they could then handle many more clients using the same number of employees. 

    Users who are not proficient in accounting would miss a mistake, go off in the wrong direction for months and be angry at the software for ruining their books.

    0Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    8mo

    @Drew Sygit probably going to have to reach some kind of scale in order to keep costs down. And to be honest I haven't gotten into those details yet. I primarily have been thinking about what would be the ideal set of features.

    Great point though!

    0Reply
  • Michael Murphy
    Investor · Buffalo · Member since 2025 · 45 posts · 27 votes
    8mo

    I personally hate the AI feature of QBO.  QBO is cumbersome enough without AI and I literally get bored in between entries waiting for the screen to update.  With AI it is even worse.  Most of the suggestions that it makes for categories are nonsense.  I really think QBOs AI costs time.  It is quicker for me to enter the category based on memory than to evaluate what AI thinks and decide to keep it or not.

    As far as parts of QBO go that are particularly tedious, the Create Sales Receipt, Create Deposit, Post Transaction on Bank Feed, and then Reconcile Bank Account rigamarole is horrible.  When you account for screen loading time it can literally take minutes to record one transaction.  I don't know if that is something that AI can help with or if it is a broader accounting software issue.

    Whatever you decide to do with the AI side, if you could make something that could run fast and something where you can use the keyboard shortcuts more easily I think that would be helpful for experienced bookkeepers.

    1Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    8mo

    @Michael Murphy completely agree. The QBO screens are frustratingly slow. Based on their current app I kind of guessed that there was no way they were going to do AI agents right.

    1Reply
  • Andrew Ferguson
    OP
    Investor · Columbus, OH · Member since 2019 · 16 posts · 7 votes
    6mo

    So to bring this full circle. I worked pretty hard at this the last few months and it's working pretty nicely. Would love to get any feedback anyone has or any feature suggestions. Future features would be like quickbooks and google drive integrations. All of that will be coming. For now, here is a loom (demo video). Feel free to comment.

    Here also is the app. You can sign up and try for free. https://www.luca-app.io/register

    0Reply
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