Experiences/referrals for Tax Planning & Strategy CPA’s that specialize in STR

Houston, Texas
Tax, SDIRAs & Cost Segregation
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Experiences/referrals for Tax Planning & Strategy CPA’s that specialize in STR

Ross Derouen
Member since 2021 · 9 posts · 15 votes

I’m looking for a CPA who specializes in short-term rental real estate, tax planning and tax strategy.

I’m currently considering the following companies and would love to hear about your experiences with:

   Hall CPA

   Keystone CPA

   Ryan Bakke / Tax Strategy 365

   WCG CPAs & Advisors

   ProVision

   Madsen & Company

   Taxstra

If you’ve worked with any of these firms, would you recommend them? How was their communication, tax planning, responsiveness, and overall experience?

Also, are there any other STR-focused CPA firms you’d recommend that I should consider?

Thanks in advance for any feedback!

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Brooklyn Humphrey
Santa Rosa Beach, FL · Member since 2026 · 5 posts · 2 votes
2mo

Hi Ross! I've been in tax accounting for about 10 years and have been a real estate agent for the past 2 years. I previously worked at Keystone CPA, and I'd definitely recommend them. They have a great team that's very knowledgeable when it comes to short-term rental taxation, tax planning, and tax strategy. One thing I always appreciated was how much they value accuracy and take the time to make sure things are done right. If you're looking for a firm that understands both the tax side and the investment side of real estate, they're a great resource.

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  • Brooklyn Humphrey
    Santa Rosa Beach, FL · Member since 2026 · 5 posts · 2 votes
    2mo

    Hi Ross! I've been in tax accounting for about 10 years and have been a real estate agent for the past 2 years. I previously worked at Keystone CPA, and I'd definitely recommend them. They have a great team that's very knowledgeable when it comes to short-term rental taxation, tax planning, and tax strategy. One thing I always appreciated was how much they value accuracy and take the time to make sure things are done right. If you're looking for a firm that understands both the tax side and the investment side of real estate, they're a great resource.

    1Reply
  • Janet Behm
    Accountant · West Jordan, UT · Member since 2017 · 182 posts · 95 votes
    2mo

    Ross, please give Lynn a call.
    He has a referral to a Certified Tax Planner, who specializes in real estate strategies. 
    Lynn is my marketing guy. Please go to my Utah Real Estate Accountants site for his phone number. Ask for the referral info.

    1Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    2mo

    Ross, I'd look beyond whether a firm simply prepares returns for STR owners. The bigger question is whether they help you plan before year-end, while there is still time to act.

    I’d ask how they handle average guest stays, material participation, time logs, cost segregation, passive-loss limitations, and placed-in-service timing. I’d also ask who you’ll actually speak with during the year, how often planning meetings happen, and whether they help implement the strategy or just hand you a list of recommendations.

    A good STR-focused CPA should be able to explain why a strategy applies to your situation, what records you need to maintain, and where the audit risks are without making everything feel overly complicated.

    Happy to connect!

    [email protected]941-914-7779
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  • Eric Foley
    Member since 2026 · 1 post · 0 votes
    2mo

    Hi Ross , i had the same question last year . You get partial exclusion for the years you lived there, but the STR years are still taxable. I've used Maven for a cost seg study and it helped offset things nicely.

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  • Kristine Nguyen
    Accountant · San Francisco, CA · Member since 2026 · 7 posts · 2 votes
    2mo

    Ross - Those firms are reputable however, i would make sure whoever you connect with specializes in real estate tax and short-term rentals for report and planning. There are a few key areas they should be covering:

    1. Personal use: Is the property also used as your primary or vacation home? Significant personal use could trigger the §280A vacation-home rules and limit deductible losses. Thus would render STR useless.
    2. Average guest stay: Is the average guest stay 7 days or less? If so, the property can potentially meet STR requirements.
    3. Material participation: Do you materially participate? For example, you may qualify if you do substantially all the work, or spend more than 100 hours and at least as much as anyone else, or spend more than 500 hours on the activity.

    If the requirements above are met, STR losses may be nonpassive and potentially offset W-2 or business income. Pairing this with cost segregation, particularly for a newly purchased or renovated property, can potentially accelerate depreciation and generate a larger first-year tax deduction.

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  • Diana KhanPro Member
    Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 613 posts · 208 votes
    1d
    Quote from @Ross Derouen:

    I’m looking for a CPA who specializes in short-term rental real estate, tax planning and tax strategy.

    I’m currently considering the following companies and would love to hear about your experiences with:

       Hall CPA

       Keystone CPA

       Ryan Bakke / Tax Strategy 365

       WCG CPAs & Advisors

       ProVision

       Madsen & Company

       Taxstra

    If you’ve worked with any of these firms, would you recommend them? How was their communication, tax planning, responsiveness, and overall experience?

    Also, are there any other STR-focused CPA firms you'd recommend that I should consider?

    Thanks in advance for any feedback!

    @Ross Derouen, I haven't personally worked with the firms you listed, so I can't recommend one over another. But I'd look for a CPA who regularly works with short term rental investors and offers tax planning throughout the year, not just tax preparation. I'd also ask how often you'll be able to speak with them and what support is included in their fees.

    I'm a real estate attorney and investor based in Maryland, and I work with clients on property transactions, contracts, and business matters. I've seen how important it is to have the right professionals involved, especially when investors are making decisions that can affect their properties and finances.

    I appreciate you bringing this up, @Ross Derouen. Finding professionals who understand real estate investing can make a big difference. It's closely related to the work I do, and I'd be happy to stay connected!

    [email protected]240-266-0291
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