Day 2 as a property investor - get a CPA

Day 2 as a property investor - get a CPA

Pittsburgh · Member since 2023 · 28 posts · 20 votes

A lot of advice I've gotten is that a CPA isn't strictly necessary when starting out, but there are a few reasons I want to make it a priority.

-- We do already have one property in service (our old primary residence) and there's still time in 2025 to maximize deductions against its income. Pretty sure I'd butcher that process if we try filing through TurboTax again. 

-- A focus of my family's 2026 investing strategy is tax efficiency. I want to make sure our record keeping, bookkeeping, and ongoing W2 withholdings are all fully IRS-compliant from day 1.

-- Bring another expert onto my team, who can help maximize the overall strategy.

Now, how much to spend and for what services ...

Why am I posting these? 
Just trying to keep myself accountable as a new investor, flesh out my ideas in writing, and hopefully spark a few good conversations that I can learn from! 

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Bill HamptonBusiness Member
Accredited Investment Fiduciary, AIF®, Financial Planner, Tax Strategist, Real Estate Investor · Atlanta, GA · Member since 2012 · 2k+ posts · 977 votes
9mo

@Matthew Samson

Posting is a great idea to keep yourself accountable. 


Adding someone to your team who can help with tax strategies and improve your credit score is also a great move. 

Make sure the person you hire is skilled in both areas. 

Happy to answer any questions. 

Hampton Tax and Financial Services LLC4.7106 Reviews
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  • Bill HamptonBusiness Member
    Accredited Investment Fiduciary, AIF®, Financial Planner, Tax Strategist, Real Estate Investor · Atlanta, GA · Member since 2012 · 2k+ posts · 977 votes
    9mo

    @Matthew Samson

    Posting is a great idea to keep yourself accountable. 


    Adding someone to your team who can help with tax strategies and improve your credit score is also a great move. 

    Make sure the person you hire is skilled in both areas. 

    Happy to answer any questions. 

    Hampton Tax and Financial Services LLC4.7106 Reviews
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    9mo

    I love the attitude - both to post and to reach out to professionals early on in the journey. You understand that there's a lot at stake and you want to make sure you get everything in place the first time. 

  • Jake BakerBusiness Member
    Flipper/Rehabber · San Diego, CA · Member since 2020 · 1k+ posts · 694 votes
    9mo

    @Matthew Samson

    Good move thinking about a CPA early. When you already have a property in service, having a pro handle depreciation and year-end strategy can easily save more than it costs. A real-estate-focused CPA and bookkeeper can set up your records correctly, keep W-2 and rental activity aligned, and help you stay fully compliant as you scale.

    Costs vary, but most new investors start with basic monthly bookkeeping and an annual tax strategy session. The key is finding someone who works with investors regularly so you’re building on a clean foundation from day one.

    BookkeepingRE - Bookkeeping for Real Estate & Service-Based Businesses58 Reviews
  • Accountant · 100% Remote · Member since 2019 · 495 posts · 215 votes
    9mo

    Hey @Matthew Samson, I hired an REI-savvy CPA after purchasing my 1st duplex rental. I think it's great to get this key relationship in place as early as possible, especially if you plan to continue purchasing rentals. There's a lot to be taken advantage of in the tax code but it has to be done correctly. A good REI-savvy tax pro can help you with all of it and they'll save you way more money than they charge (typically).

    If you don't have one, I'm happy to send over the list my bookkeeping firm recommends (all REI-savvy since 100% of our clients are REIs).

    - Time Capital Bookkeeping (REI since 2019)

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