Looking for an STR Tax Strategist/CPA (Self-Managed LLC + W-2 Offset Strategy)

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Looking for an STR Tax Strategist/CPA (Self-Managed LLC + W-2 Offset Strategy)

Scott Spungin
New York City · Member since 2018 · 6 posts · 1 vote

Hi everyone,

I am looking for recommendations for a real estate-focused CPA or tax strategist who specializes in short-term rentals (STRs).

My portfolio and strategy profile:

  • Entity Structure: Single-property held in an LLC, with concrete plans to scale and add more properties under this structure soon.

  • Operations: I handle 100% of the day-to-day guest communication and cleaning coordination myself.

  • Bookkeeping: I track all income, expenses, and property-level metrics using Baselane.

  • Core Tax Strategy: My primary goal this tax year is utilizing the STR tax loophole to legally offset my W-2 income, including executing a cost segregation study for accelerated depreciation.

What I am looking for in a professional:

  • Deep, specialized knowledge of the 7-day rule and defending material participation hours under IRS scrutiny.

  • Comfort working with modern real estate fintech (like Baselane) rather than demanding manual spreadsheets.

  • A forward-looking partner who offers proactive quarterly or mid-year strategy sessions, rather than just once-a-year filing.

If you love your STR accountant or if you are a CPA specializing in this exact framework, please drop your recommendations below or shoot me a DM. Thank you!

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Scott E. FlemingBusiness Member
CPA · United States · Member since 2026 · 8 posts · 11 votes
3d

@Scott Spungin, at the risk of being self-promoting, allow me to offer our help. We're a real estate focused CPA firm with approx. 80 clients who own an average of 12 properties each. My business partner was a senior manager with Wells Fargo for 15 years, and I was a real estate broker for a decade before becoming a CPA. We may be able to help. 

662-205-6333
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  • Scott E. FlemingBusiness Member
    CPA · United States · Member since 2026 · 8 posts · 11 votes
    3d

    @Scott Spungin, at the risk of being self-promoting, allow me to offer our help. We're a real estate focused CPA firm with approx. 80 clients who own an average of 12 properties each. My business partner was a senior manager with Wells Fargo for 15 years, and I was a real estate broker for a decade before becoming a CPA. We may be able to help. 

    662-205-6333
    S E Fleming CPA51 Review
    WebsiteView Page
    1Reply
    • Scott Spungin
      OP
      New York City · Member since 2018 · 6 posts · 1 vote
      7h

      Scott- Can you tell me more about your services and where you are based? In all, I'm looking for bookkeeping assistance (I use Baselane), tax planning and strategy, and a cost segregation analysis. Thank you in advance for your time.

      0Reply
  • Min JangPro Member
    Accountant · Member since 2026 · 5 posts · 2 votes
    3d

    Scott, this sounds like a situation where the details need to be coordinated carefully—especially whether the loss will be usable, cost seg timing, and material participation records.

    Our firm works with rental property owners, and I’d be happy to have an initial conversation to learn more and see if we might be a good fit.

    1Reply
    • Scott Spungin
      OP
      New York City · Member since 2018 · 6 posts · 1 vote
      7h

      Min- Thank you for reaching out. I'd like to learn more. What is your availability over the next few days?

      0Reply
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    3d
    Scott - would love to see if we’re a good fit. I have many clients with STRs and have had some good results for them. I also have a spreadsheet I can send to you to document your material participation hours. Pm me if you’re interested in connecting (we can not solicit for services in the dms but can comment on this post because it was in the classfied section)
    [email protected]
    Brick House CPAs53 Reviews
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  • Julius VincentBusiness Member
    Tax Strategist | CPA, MBA + Wharton FP&A | CFO-Level Planning · Houston, TX · Member since 2025 · 157 posts · 172 votes
    3d

    Hi @Scott Spungin - Lots of good CPAs here. I'm also a real-estate focused tax strategist with a number of clients that I guided through the STR loophole last year. Feel free to book a call here: https://go.horizonwealthtax.com/call

    In the meantime, here are a couple nuggets that a lot of CPAs miss:

    1) If you're married, your spouse's hours count toward material participation with yours, even though they don't for REPS.

    2) When you add the next property, there's also a grouping decision that's much easier to get right in year one than to fix later.

    [email protected]281-407-7353
    Horizon Wealth & Tax Advisors510 Reviews
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  • Tim JohanssonBusiness Member
    Member since 2026 · 3 posts · 0 votes
    1d

    Hi @Scott Spungin. Please note that you can only combine both spouses real estate hours for material participation. Real estate hours can not be combined to achieve real estate professional status (REPS). I highly recommend all of my clients have a STR in their portfolio as REPS is evaluated on a year-by-year basis. If I achieve REPS in 2026, it doesn't automatically qualify me for REPS in 2027. This is why I recommend a STR in an investor's portfolio as those consistent hours spent on a STR will provide hopefully plenty of hours to achieve REPS. The grouping election (treating all of your investment properties as a "single activity") is a must for any taxpayer wanting to achieve REPS. I have many clients looking to acquire a STR before year-end and we provide an estimate of their tax savings before even acquiring the property. @Scott Spungin, happy to assist you in identifying which property would provide you the most significant tax deduction.

    [email protected]
    RE TAX PROS LLC54 Reviews
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    • Scott Spungin
      OP
      New York City · Member since 2018 · 6 posts · 1 vote
      7h

      Tim - Thank you for reaching out. I'd like to learn more. What is your availability over the next few days?

      0Reply
  • Kristine Nguyen
    Accountant · San Francisco, CA · Member since 2026 · 7 posts · 2 votes
    1d

    Hi @Scott Spungin If you're investing in New York, location matters a lot for an STR strategy. NYC has particularly restrictive rules that generally require the host to live in the unit and be present during stays of less than 30 days. That may create a separate §280A vacation-home/personal-use issue, which could limit your ability to use cost segregation deductions to generate a loss against W-2 income.

    Outside NYC, STRs can be more feasible, but the rules vary by city, town, and county. I would confirm the local zoning, permitting, registration, and occupancy requirements before purchasing a property or completing a cost seg based on an STR strategy.

    We work with STR and rental owners on tax planning and compliance throughout the real estate lifecycle—from acquisition and refinancing through sale or 1031 exchange. I'd be happy to have an initial conversation and learn more about your portfolio.

    0Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    43m

    Scott, this is exactly the kind of STR setup where I'd want the tax strategy, bookkeeping, material-participation documentation, and cost segregation all coordinated together, not handled as separate items at year-end.

    The first thing I’d look at is whether the property actually meets the short-term-rental classification you’re relying on. The 7-day average-stay rule can take the activity outside the normal rental-activity bucket for passive-loss purposes, but that alone does not automatically make the losses usable against W-2 income. You still need to materially participate.

    Since you’re self-managing and handling the day-to-day guest communication and cleaning coordination, that may put you in a good position, but I’d document it contemporaneously. If you’re relying on the 100-hour-and-more-than-anyone-else test, I’d also reasonably track the hours of cleaners, co-hosts, contractors, or anyone else working on the property so you can substantiate that nobody participated more than you.

    Cost segregation can be very powerful here, but I’d only do it after confirming that the resulting losses are actually usable. The order matters: classification, participation, placed-in-service timing, cost seg, and documentation.

    I also agree with your point about wanting proactive planning. For an STR strategy like this, I'd want the CPA involved before year-end to review hours, average stay, projected income, improvements, furnishings, and whether the strategy is still on track rather than discovering an issue when the return is already being prepared.

    Feel free to DM me, I'd be happy to send over a few STR tax and material-participation resources that might help you vet the strategy and the CPA relationship.

    [email protected]941-914-7779
    INVESTOR FRIENDLY CPA®5241 Reviews
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