Bookkeeping for 9 units

Pittsburgh Metro
General Real Estate Investing
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Bookkeeping for 9 units

Tim Wiegand
Member since 2018 · 1 post · 1 vote

Hi guys- I've got two mulit's (9 units total) but am struggling on the bookkeeping side. Id appreciate any guidance on how to affordably proceed. I've got my CPA doing my bookkeeping, but she's frustrated with how messy things are- I did switch PM's this year and my original PM had terrible books. I also use Stessa (free version) to track all my bank account - I have my properties under my LLC and funds go in and out of one acct for both properties. I go into Stessa regularly and identify expenses, capex etc, but it seems Stessa is confusing things with the PM reports and my bank accounts with my CPA/Bookkeeper.

What do other small investors do for bookkeeping? Hire someone or do themselves? If hiring, what do you look for and how much should it cost?

I’ve interviewed a few firms that do “bookkeeping” and they want $300-500 a month, which is a big hit to my P&L.

Appreciate any guidance. I realize I can’t scale until I figure out my bookkeeping and really getting my financials in order.

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  • John Cafarelli
    Member since 2026 · 13 posts · 3 votes
    1d

    Tim, I hit this same wall at eight units, and the fix wasn't a better app - it was stopping the double-counting. My PM statement and my bank feed were both creating income and expenses, so nothing ever tied out and my CPA was constantly asking questions.

    What finally worked for me: I gave each property its own checking account, even though they're under one LLC. Rent and PM deposits go in, and only that property's bills come out. In Stessa I connect just the bank accounts, not the PM portal, and I use the PM statement only as a cross-check at month-end.

    I also do a 20-minute Friday routine. I categorize that week's transactions while I still remember them, snap a photo of any paper receipt, and rename vague charges - "Home Depot $84" means nothing in March. At month-end I reconcile each account to the bank balance before I send anything to my CPA.

    I wouldn't hire a $300-500/month bookkeeper until that setup is clean for two months. Otherwise you're paying someone to untangle the same mess every month.

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    • Eric Kleinsasser
      Specialist · PA · Member since 2026 · 43 posts · 10 votes
      1d

      Good thoughts John, thanks for sharing. How do you keep track of everything? Do you use an app or just sheets?

      0Reply
  • Eric Kleinsasser
    Specialist · PA · Member since 2026 · 43 posts · 10 votes
    1d

    Hey Tim, with two multis sharing one LLC account, a common cause of this mess is that deposits and repairs don't get tagged to a specific property before your CPA and the PM report ever meet. Then Stessa ends up as a third version of the numbers.

    Some things that may help before you jump to a $300–500 a month firm:

    1. Tag every Stessa transaction to a property the same day it clears. Even a temporary "Building A / Building B" is enough.

    2. Once a month, match three things: the bank statement, Stessa, and the PM's rent roll or owner statement. Anything that doesn't match gets a note that month.

      We build custom software to help with problems like this. If there is anything we can do to help to make your life easier, reach out to me and we can have a conversation.

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  • James JonesPro Member
    Investor · Collierville, TN 38017 · Member since 2017 · 1k+ posts · 683 votes
    1d

    At 9 units you are at the exact point where a spreadsheet stops working and the books start lying to you. I run 236 properties in Memphis, and the rule is the same at 9 as at 236: every property gets its own tracking, every dollar gets a category, and rent, rehab, and refi money never mix.

    Do not wait until tax time to find out a property lost money. Reconcile every month, even if it is just you and a simple ledger to start. The number that matters is cash flow per property after all costs, not what hit the bank account that month.

    The $300-$500 a month you mentioned is real money at 9 units - that is $3,600-$6,000 a year. Spend it on a system you will actually use every week, not the fanciest one.

    What are you using now - spreadsheet, software, or nothing yet?

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  • Dan Worth
    Pittsburgh, Allegheny County · Member since 2026 · 71 posts · 25 votes
    1d

    The biggest fix is probably giving each building its own bank account, even inside the one LLC. When both properties run through one account, Stessa, the PM statements and your CPA are all trying to split the same transactions after the fact, and that's where the confusion and double counting come from. I'd also pick one source of truth for rent and PM-paid expenses, usually the PM's monthly owner statement, and book it as one deposit with the fees and repairs broken out, instead of letting the bank feed and the PM report both bring in the same items. For this year's mess, ask the old PM for a full ledger export and have your CPA do a one-time cleanup; after that, a monthly half-hour reconciliation on your end may be all 9 units need, rather than a $300-500 monthly service.

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  • Sundeep Babbar
    Real Estate Coach · Austin · Member since 2022 · 21 posts · 8 votes
    1d

    Tim, the mismatch between the PM reports and the bank is usually because the PM deposits net. Rent comes in gross, the management fee and any repairs they paid come out, and only the net hits your account. If Stessa just sees that net deposit it will never tie to the owner statement your CPA is reading, so book it as gross rent minus each fee and repair line from the statement. I'd ask your CPA if that's how they want it before you redo past months.

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  • Divin KanyamaBusiness Member
    Accountant · Seattle, WA · Member since 2025 · 671 posts · 285 votes
    1d

    @Tim Wiegand I’d separate the cleanup from the ongoing bookkeeping before committing to another monthly bill. With a PM change and overlapping records, I’d first ask your CPA to walk through one month with you and identify exactly where things stop matching. One thing to check: the PM’s net payout isn’t the same as gross rent, so recording that deposit as additional income alongside the PM’s detailed activity could double-count it. I’d agree on one main set of books, consistent property labels, and a process for matching the PM statements to the bank activity. Separate accounts might make tracking easier, but they won’t fix duplicate entries or missing PM records.

    For hiring, I’d look for someone who can explain how they reconcile PM statements, track each property, and handle manager-held reserves, deposits, and capital improvements—not just categorize bank transactions. I’d request a fixed cleanup quote and a separate ongoing quote based on your actual transaction volume and reporting needs. I wouldn’t call $300–$500 reasonable or excessive without knowing what’s included. To keep costs down, I’d consider handling receipts and routine categorization yourself, with a rental-property bookkeeper doing the monthly reconciliation and your CPA handling tax questions and periodic review. Get those roles agreed upfront so you’re not paying two people to redo the same work.

    [email protected]
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  • Matthew Tregoning
    Property Manager · Melbourne, FL · Member since 2019 · 551 posts · 188 votes
    1d

    Since the manager changed this year, I’d ask your CPA for a specific missing-records list and have each PM answer for its own period. From the management side, I’d package the statements, supporting invoices and handoff records by property and month, with unresolved questions in one list. Otherwise you can spend a lot of time recategorizing transactions while the document needed to explain them is still missing.

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  • BJ Everson
    Realtor · Columbus, Franklin County · Member since 2026 · 106 posts · 31 votes
    1d

    Tim, I hit the same wall once two buildings shared one account — Stessa, the PM statement and the CPA were reconciling three different stories. What cleaned it up for me without a $500/mo firm: one operating account per building (same LLC is fine), book gross rent and fees separately so net deposits don't fake your income, and make the owner statement the source of truth for rent/fees while the bank feed only confirms cash. Capex gets its own category so it doesn't look like a bad month of repairs. At 9 units you're big enough for clean books and still small enough to DIY the cleanup with your CPA for one closed month, then decide if a cheaper bookkeeper is worth it. Are both buildings on the new PM now, or is one still on the old reports?

    0Reply
  • Muyees Ayilara
    Lender · Boynton Beach, FL · Member since 2026 · 182 posts · 73 votes
    21h

    Tim, I see this a lot with investors at your size, and you are right - you cannot scale until the books are clean.

    The biggest issue I see in your setup is one bank account for both properties and mixing Stessa, the PM reports, and your CPA. That is why everything is confusing. No software will fix that until the money flow is clean.

    This is what I would do for 9 units:

    1. One bank account per property, or at least one operating account per LLC. Do not run both properties through one account. Your CPA needs to see each property stand on its own.

    2. Pick one system of truth. If you like Stessa, use Stessa and stop trying to reconcile it against the PM reports every month. Let the PM handle rent collection and maintenance, and you track it in Stessa from the bank statements. If you outgrow Stessa, QuickBooks Online with a real estate bookkeeper is the next step, but do not run both at the same time.

    3. For $300-$500 a month, that is actually normal for a real estate bookkeeper for 9 units, but you should not be paying that just for someone to categorize transactions. You should be getting monthly P&Ls by property, a clean balance sheet, and a year-end package your CPA can use without rebuilding everything. If they are not giving you that, it is not worth it.

    4. If you hire someone, hire a bookkeeper who only does real estate investors. Ask them how they handle security deposits, owner draws, capex vs repairs, and PM statements. If they cannot answer those clearly, keep looking.

    The PM switch is what hurt you. Get the old PM's final statements, close that chapter, and start fresh with the new PM from this month forward. Do not try to go back and fix a full year of bad PM books in Stessa - it will drive you crazy.

    You are not far off. Clean accounts, one system, and a monthly close by the 10th will fix most of this.

    0Reply
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    14h

    I’d personally continue to use Stessa if it’s working. If you have a pm, you’d plug in monthly numbers from them and then add anything not captured such as ITI, professional fees, etc.

    [email protected]
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  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · Sarasota, FL · Member since 2017 · 5k+ posts · 3k+ votes
    10h

    Tim, with 9 units, I think you're at the point where having clean property-level books is worth paying for rather than continuing to spend your own time fixing everything.

    One thing I'd change is making sure every transaction can be clearly tied back to the specific property. Having both properties running through one account isn't necessarily impossible to manage, but it makes reconciliation and tax reporting much harder as the portfolio grows.

    I'd also make sure the bookkeeper has a clear process for separating repairs, improvements/capex, owner contributions and distributions, and property-level expenses. That's where a lot of the tax headaches tend to start.

    I wouldn't necessarily choose the cheapest $300–$500 option either. I'd ask how they handle property-level reporting, bank reconciliation, capex tracking, and communication with your CPA.

    At 9 units, the goal should be to give your CPA clean books that are actually ready for tax planning, not just a spreadsheet of transactions.

    If you'd like, I can share a few things I'd look for when evaluating a real estate bookkeeper.

    [email protected]941-914-7779
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  • Victoria Ajah
    Member since 2026 · 11 posts · 2 votes
    5h

    Tim, before you decide whether to hire or do it yourself, it helps to split this into two jobs: a one-time cleanup and a monthly routine. For the cleanup, pick one recent month and line up the bank statement, the PM owner statement and what Stessa shows, then mark every line that does not match. Most mismatches come from a few repeat causes, like net rent deposits or repairs the PM paid out of rent, so one month usually shows you the pattern for the whole year. Hand that list to your CPA and she can tell you which fixes she needs from you and which she can make herself. Once the books are clean, the monthly routine is much smaller, and the hire or DIY choice gets a lot easier to price.

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  • Andrew KimBusiness Member
    Rental Property Investor · Across the US · Member since 2026 · 14 posts · 3 votes
    4h

    $300-500 a month is $33-55 a door, every month?? yikes. for what’s mostly a matching job once the accounts are set up. and, you’re already doing half of it yourself, going into stessa to tag every expense and capex item by hand. for ongoing, there are really three price points: stessa free (what you have now), a software tier that categorizes and matches the PM statements against the bank for you, or a human bookkeeper at the quotes you got. our software is the middle one. entry tier is priced like a premium stessa plan, so nowhere near bookkeeper money. the cleanup of the switch year is a separate one-time job either way, so quote it separately.

    PocketAM - Landlord Accounting Software
    WebsiteView Page
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  • Ken B.
    Investor · Fairfax Station, VA · Member since 2012 · 6 posts · 1 vote
    3h

    Tim, the replies cover the monthly routine well. Two things specific to changing managers mid-year are worth settling first, because they're often what keeps a CPA frustrated.

    1. Tie out the handoff. Get the old manager's final owner statement and write down three balances as of the transfer date: security deposits, any reserve they held, and what they still owed you. Then confirm each one arrived, either at the new manager or in your account. Deposits matter most: you still owe them to tenants whether or not the money made the trip, and they belong on the books as a liability, not income.

    2. Tie gross rent to the 1099s. With two managers you'd normally get two 1099-MISCs for 2026, so ask both how they'll report. Your gross rent should reconcile to the total. The usual gaps are rent collected in December but paid to you in January, which generally counts in the year the manager received it, and fees netted out of deposits. Have your CPA confirm the treatment.

    On cost, I'd do both before taking more quotes. A bookkeeper pricing a messy handoff has to price in the unknown, so a defined cleanup list should get you a firmer number and show what's really left to do each month.

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  • Bill B.
    Investor · Las Vegas, NV · Member since 2013 · 8k+ posts · 10k+ votes
    3h

    Using quicken I can manage the finances of a dozen properties myself in half an hour, MAYBE an hour a month. There’s zero chance I would pay someone to do it for me. One, I like doing it. Two it gives me a chance to see mistakes, late lays, repairs and so on in an overview for the month. Three, who would do it for less than $50 for all 12?

    It auto downloads all bank and credit card transactions, memorizes payees and schedules bills. There’s just about zero effort required. You’ll have reports by any date range, by property or by category. You SHOULD end up saving on tax prep at yer end if you’re paying by the hours and just stacks on top of not paying a bookkeeper. I would say 20 properties should be pretty easy and not take any longer. MAYBE at 40 or 50 properties if you don’t like doing it and don’t have 2 spare hours a month you could show someone your process and pay $100or if they’re related $200 to do it for you.

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  • Ming Yi
    Investor · San Francisco · Member since 2026 · 51 posts · 24 votes
    23m

    With 9 units across two multis, the fix is structure, not more hours. First, separate the money: one operating account per property, or at minimum one per building, with rent going in and every expense coming out of it. If the CPA is frustrated, it is almost always because personal and rental money are mixed or because expenses land in one pile with no property tag. Second, use a chart of accounts that matches Schedule E categories: rents, repairs, insurance, taxes, utilities, management, depreciation. If every transaction is tagged to a property and a category when it happens, the year-end P&L practically writes itself. Third, do a monthly close, even a simple one: reconcile the bank account, check that every deposit matches a lease, and flag anything uncategorized while you still remember it. An hour a month beats a painful week in January. Switching PMs midstream is exactly when books get messy, so ask the old PM for a full transaction export and reconcile it against your bank statements before you let it go.

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