Accounting for RE Pro with bookkeeping, payroll, and taxes
Kassidy BensonBusiness Member
Professional · Denver, CO · Member since 2015 · 15 posts · 6 votesAccounting for RE Pro with bookkeeping, payroll, and taxes
Most Popular Reply
Simon W.Business Member
Real Estate Consultant · Lehigh Valley PA & New York City · Member since 2013 · 1k+ posts · 662 votes$500-$625/mo sounds reasonable, but it depends how much work is actually involved.
When I charge my clients, there isn't like a flat rate I do across the board because each client is different. I would need to check the books and then propose a price.
I get the “AI will replace bookkeepers/accountants” argument, but I think it misses the core reality of what accounting actually is in practice: It is constantly a gray and depends on context that rarely lives inside the transaction itself.
A bank feed line item is just a line item. Example: Payment to an attorney
Most of the time, sure, it’s legal fees. But it could just as easily be:
- an escrow/retainer for a lawsuit (expense),
- a real estate closing-related cost that gets capitalized,
- a down payment being held in trust (balance sheet),
- reimbursement for something paid on behalf of the business,
- or something that needs owner/shareholder classification depending on who benefited.
AI can guess, but it can’t *know because the “reason” is not in the merchant name, amount, or memo. The correct treatment often comes from:
- the engagement letter / invoice detail,
- the underlying contract,
- who the beneficiary was (business vs owner),
- timing, intent, and materiality,
- and sometimes just a quick conversation with the client.
And that’s why good bookkeeping/accounting isn’t “data entry.” If you strictly hire someone called a bookkeeper and all they do is bookkeeping, then I see why the lower price tag is more intriguing. It’s judgment, documentation, and defensible classification. AI will absolutely help with automation (coding suggestions, anomaly detection, faster reconciliations), but the *accountant’s job* is to translate messy reality into clean financials that won’t fall apart under scrutiny.
So yeah—AI will change the workflow. But replacing humans entirely? Not when the job is fundamentally interpretation + accountability, not just categorization.
17 Replies
- 7moBrandon VukelichBusiness MemberReal Estate Broker · Tacoma, WA: 🏢 27 LTRs 🏡 3 STRs · Member since 2018 · 546 posts · 456 votes
Hi @Kassidy Benson your situation sounds identical to mine. I'm an owner/broker that is setup as an S-corp with one w-2 employee (my wife) and I pay monthly taxes. Honestly, QB online is still the way to go but too much for someone like you or me to manage. I have a 3rd party bookkeeper. She was great at $300/mo for the last two years but just bumped me to $500/mo so I'm shopping again. I don't know your biz 100% but $625/mo seems excessive, especially if your CPA has your annual tax return business as well but again, I'm not privy to the work load. Maybe managing your 5 rentals adds to it but if they are STRs, I do know that adds to BK hours to reconcile vs LTR properties. I have a 3-unit STR (sep LLC) that I run on its own QB account and my BK charged $300/mo for that company. She also just bumped it to $405/mo. BTW, nothing changed in either business. She just said she reevaluated the work load and had been undercharging me.
In my recent vetting of new BKs, one told me they admit they are going to be extinct soon as AI can reconcile books very easily for most small businesses. I'm not quite there on the trust level for AI yet but this is another reason why I'm a little put off my the big rate hikes by my BK. I'm assuming they could be or should be using AI to make their jobs easier so I don't believe the huge increase is justified or warranted. Best wishes on your plan!
Broker at Multifamily Properties519 Reviews - Professional · Denver, CO · Member since 2015 · 15 posts · 6 votes7mo
Thanks for your reply Brandon. I'm thinking of trying Wave. It's $200/year. https://www.waveapps.com/ or https://www.xero.com/us/
I don't send any invoices, but I think once I categorize an expense it will remember it for the next month automatically so I don't have to pay a bookkeeper. Most of my expenses are recurring.
My partner is a plumber, he uses QB and loves it. IDK why I have such a hard time using it.
- 7moWilliam WhitleyBusiness MemberAccountant · TN · Member since 2025 · 144 posts · 91 votesGood afternoon, Kassidy, I know quite a few real estate investors who use QBO for a multiple property portfolio. If it is set up correctly and you have someone well versed in QBO for real estate investments that can provide you some guidance and training, I think you would find it to be a good platform. The main thing is to get it customized correctly for your portfolio and get some initial guidance on it. Then you could elect to manage the bookkeeping without hiring a bookkeeper or you could explore a hybrid approach where you have an experienced real estate investment bookkeeper provide monthly consultation on an as needed basis.
- 7moAaron ZimmermanBusiness MemberAccountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
Are the rentals reported on Schedule E or are they in a multi-member LLC?
I'd recommend Gusto for payroll (they will handle all payroll tax filings).
I'd recommend QB online for your S Corp since you will need to have an income statement and balance sheet.
Since I recommend QB online for your S Corp, you'll likely want to use QB online for the properties but in a separate QB file. You'll need to have the properties reported by class because each property needs to be reported individually on the tax return.
Brick House CPAs53 Reviews- Professional · Denver, CO · Member since 2015 · 15 posts · 6 votes7mo
Quote from @Aaron Zimmerman:
Are the rentals reported on Schedule E or are they in a multi-member LLC?
I'd recommend Gusto for payroll (they will handle all payroll tax filings).
I'd recommend QB online for your S Corp since you will need to have an income statement and balance sheet.
Since I recommend QB online for your S Corp, you'll likely want to use QB online for the properties but in a separate QB file. You'll need to have the properties reported by class because each property needs to be reported individually on the tax return.
Thanks! One thing I don't like about my current situation is having the payroll separate. they were using Paychex and I had a separate login to that system. They used Qiuckbooks plus another software called Taxdome. I do not like having it all separate. Wave has everything in one platform, that is what I'm leaning towards. Appreciate your feedback!
- 7moAaron ZimmermanBusiness MemberAccountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
@Kassidy Benson Taxdome is a client facing app your accountant uses. I use it personally!
I totally understand the frustration with having multiple log ins. I don't have a great solution. I'll have to look into wave post tax season. Thanks for sharing!
Brick House CPAs53 Reviews
- Accountant · Indianapolis, IN · Member since 2019 · 247 posts · 134 votes7mo
For your rentals I would use Stessa since it is free, built for real estate, and makes P&Ls easy. For the brokerage side stick with QuickBooks and add Gusto for payroll since it handles all the taxes and filings automatically. Both platforms import bank and credit card transactions so you are really just categorizing everything which is exactly what you want. That combo will run you maybe $100 a month total which is a big difference from what you are paying now. And honestly if you feel detached from your numbers at $625 a month that might be worth a conversation on its own.
- 7moSimon W.Business MemberReal Estate Consultant · Lehigh Valley PA & New York City · Member since 2013 · 1k+ posts · 662 votes
$500-$625/mo sounds reasonable, but it depends how much work is actually involved.
When I charge my clients, there isn't like a flat rate I do across the board because each client is different. I would need to check the books and then propose a price.
I get the “AI will replace bookkeepers/accountants” argument, but I think it misses the core reality of what accounting actually is in practice: It is constantly a gray and depends on context that rarely lives inside the transaction itself.
A bank feed line item is just a line item. Example: Payment to an attorney
Most of the time, sure, it’s legal fees. But it could just as easily be:
- an escrow/retainer for a lawsuit (expense),
- a real estate closing-related cost that gets capitalized,
- a down payment being held in trust (balance sheet),
- reimbursement for something paid on behalf of the business,
- or something that needs owner/shareholder classification depending on who benefited.
AI can guess, but it can’t *know because the “reason” is not in the merchant name, amount, or memo. The correct treatment often comes from:
- the engagement letter / invoice detail,
- the underlying contract,
- who the beneficiary was (business vs owner),
- timing, intent, and materiality,
- and sometimes just a quick conversation with the client.
And that’s why good bookkeeping/accounting isn’t “data entry.” If you strictly hire someone called a bookkeeper and all they do is bookkeeping, then I see why the lower price tag is more intriguing. It’s judgment, documentation, and defensible classification. AI will absolutely help with automation (coding suggestions, anomaly detection, faster reconciliations), but the *accountant’s job* is to translate messy reality into clean financials that won’t fall apart under scrutiny.
So yeah—AI will change the workflow. But replacing humans entirely? Not when the job is fundamentally interpretation + accountability, not just categorization.- Professional · Denver, CO · Member since 2015 · 15 posts · 6 votes7mo
Quote from @Simon W.:
$500-$625/mo sounds reasonable, but it depends how much work is actually involved.
When I charge my clients, there isn't like a flat rate I do across the board because each client is different. I would need to check the books and then propose a price.
I get the “AI will replace bookkeepers/accountants” argument, but I think it misses the core reality of what accounting actually is in practice: It is constantly a gray and depends on context that rarely lives inside the transaction itself.
A bank feed line item is just a line item. Example: Payment to an attorney
Most of the time, sure, it’s legal fees. But it could just as easily be:
- an escrow/retainer for a lawsuit (expense),
- a real estate closing-related cost that gets capitalized,
- a down payment being held in trust (balance sheet),
- reimbursement for something paid on behalf of the business,
- or something that needs owner/shareholder classification depending on who benefited.
AI can guess, but it can’t *know because the “reason” is not in the merchant name, amount, or memo. The correct treatment often comes from:
- the engagement letter / invoice detail,
- the underlying contract,
- who the beneficiary was (business vs owner),
- timing, intent, and materiality,
- and sometimes just a quick conversation with the client.
And that’s why good bookkeeping/accounting isn’t “data entry.” If you strictly hire someone called a bookkeeper and all they do is bookkeeping, then I see why the lower price tag is more intriguing. It’s judgment, documentation, and defensible classification. AI will absolutely help with automation (coding suggestions, anomaly detection, faster reconciliations), but the *accountant’s job* is to translate messy reality into clean financials that won’t fall apart under scrutiny.
So yeah—AI will change the workflow. But replacing humans entirely? Not when the job is fundamentally interpretation + accountability, not just categorization.I think it would be really helpful to have someone review this high level. Originally I was working directly with a CPA who understood the grey area, unfortunately she is MIA now I deal with lower level people who have access to my bank accounts and they are doing basic data entry and not well. I've started using Wave and added all my transactions. For me it's been so good to just see what I'm spending, seems crazy but I've been using this CPA for 8 years and mostly just reviewing the P&Ls. Getting in there to see each transaction is very needed after being detached, there are so many things I've been paying for that I'm not even using. I think it's going to really cut down on unnecessary spending by me managing this more hands on.
- 7moSimon W.Business MemberReal Estate Consultant · Lehigh Valley PA & New York City · Member since 2013 · 1k+ posts · 662 votes
@Kassidy Benson—I can definitely take a look on a high level for you if you like. no strings attached.
It is definitely good idea to see for yourself where your money is going, but don't dwell on learning a new set of skills when you can focus on what you do best.
Sometimes it is good to have another person look at it. I always tell my clients that while I can help them with their taxes, I still would rather have a 3rd party look at it. If you are doing everything yourself, you won't really catch your own mistakes. But some still want me to prepare it regardless haha
i tried using Wave but just doesn't tell the full picture. If you are only focused on the P&L it would make sense but as someone who is always looking at financials, I look at more than just the P&L. that's just me though.
- 7moNathan MillerPro MemberProperty Manager · Grants Pass, OR · Member since 2009 · 429 posts · 201 votes
I'd recommend a standalone payroll app (like Intuit Payroll or Gusto) for your payroll and taxes combined with a property management accounting app for your rentals. The property management accounting can pretty well take care of itself using the right software and do full business accounting, and payroll/taxes can be done separately (and imported into your PMS if needed).
You won't find any software that combines the features today and if you use QBO or Xero for property management accounting you'll be entering everything manually and keeping things like online payments and reporting away from your tenants and owners.
- 7moCliff BennerBusiness MemberAccountant · Denver, CO · Member since 2020 · 392 posts · 183 votes
Quote from @Kassidy Benson:
Hi! I'm an agent and brokerage owner in Denver. I'm looking for a software that is easy to use for bookkeeping, payroll, and rental expense tracking. My CPA is charge $625/m and I feel so detached from the income and expenses. I've tried quickbooks, but I couldn't figure it out. I also have 5 rentals that I need to track. I want it to import my bank and credit card charges. I keep everything in separate accounts, so I just need to categorize expenses and create P&L (important to get mortgages). I'm also an SCorp and have one employee - so I need to run payroll w/ taxes. Lastly I need help with monthly tax payments. What software would you recommend?
Hello Kassidy!
I see you are from Denver as well!
I understand the frustration with QBO and Accountants being detached. I will say that CPAs tend to charge more(they can with their certifcates) but also, some find the Bookkeeping portion of work to not be an area they can provide the most value.
For my clients I have a Tech Stack that I can help manage and get discounts on as well, with a focus on these softwares I am able to make sure they are set up for success and have a consistent process across my clients.
With that, I do use QBO for all my clients, mainly the Plus subscription for the Class tracking features, I set the Chart of Accounts up in a way that allows it to be easy to read, and I meet with my clients monthly to discuss their financials and make sure they are getting the information they need to make the decisions they need.
My Tech stack is; QBO, Gusto(for Payroll), and BOX. They can connect to each other, but mainly I know they perform the job well and I can get what I need from them.
Benner Stride52 Reviews - 4moBasit SiddiqiBusiness MemberAccountant · New York, NY · Member since 2015 · 8k+ posts · 3k+ votes
Do the financial statements make sense to you when you are provided year end statements?
If they do not make sense, you may want to have quarterly calls to go over the books to confirm you and the accountant are on the same page.
If you are concerned about costs, maybe you can have a chat with your accountant so your books are done on a quarterly basis instead of a monthly basis.
In regards to softwares, I recommend REIHUB for your rental properties. You can prolly continue to use Quickbooks for your S-Corp business.
Best of luck
Basit Siddiqi CPA4.979 Reviews - CPA| New Clients Welcome| 50 States · Member since 2016 · 435 posts · 93 votes3mo
@Kassidy Benson, hi. Use two systems: one for the brokerage/S-Corp and one for the rentals. QuickBooks Online or Xero can work for the S-Corp, payroll, and tax planning, while Stessa or REI Hub may be easier for rental tracking. The key is proper setup: clean chart of accounts, property tracking, bank feeds, reconciliations, and lender-ready P&Ls.
- 3moCliff BennerBusiness MemberAccountant · Denver, CO · Member since 2020 · 392 posts · 183 votes
Hi Kassidy!
That might be a reasonable amount, depending on the scope of work with monthly and annual items they may do for you.
I have all my clients on QBO, plus subscription, so we can track the financials per property and make sure they are tax ready at anytime. It does an import, lets us create a financial packet for you, and it's such a universal software in the accounting world to use. I have manually done payroll in the past, but I refer all my clients to Gusto for payroll, they automate all the payments and reports in such a way that it is worth it. I would be happy to meet with you, but I would recommend that you find someone who is willing to sit and explain each account to you and why they are doing certain things on your Books so you understand it.
I will message you so we can possibly connect
Benner Stride52 Reviews - Real Estate Consultant · Norfolk, VA · Member since 2017 · 345 posts · 201 votes3mo
@Kassidy Benson I’d probably stick with QuickBooks Online + Gusto for your setup.
Since you already have experience with QBO, I don’t think your issue is the software—I think it’s more likely that your books and workflow just need to be refined so the system actually works for you.
For your setup (agent business + S-Corp + 5 rentals + payroll), QBO should be able to handle everything well if structured properly:
- Separate classes or locations for each rental property
- Clean chart of accounts for business vs rental activity
- Bank and credit card feeds for automatic transaction imports
- Monthly P&L and balance sheet reporting (important for lenders)
- Integration with payroll and tax workflows
For payroll, I like Gusto because it integrates well with QBO and handles payroll tax filings, W-2s, and compliance pretty smoothly.
That said, software alone won’t solve the problem. The bigger issue is if you feel detached from your numbers while paying $625/month. At that price, you should have:
- Clean monthly financials
- Visibility into cash flow
- Estimated tax guidance
- A clear understanding of where your money is going
You should be able to log in and quickly answer:
- How much did my brokerage make this month?
- How profitable are my rentals?
- How much should I set aside for taxes?
If you can’t answer those easily, the process probably needs work—not necessarily a different software.
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