Tax Pro - here in Pittsburgh or elsewhere (virtual)?

Question

My wife and I are new to real estate investing - currently have three doors, two of which we are renting out (LTR + STR). We are looking for a highly qualified CPA who is very knowledgeable in handling our real estate portfolio and offering suggestions on how to save on taxes in the near term. We feel as though we should be able to defer quite a bit on our taxes this year but just want to make sure we dot our i's and cross our t's. Our other question is whether or not it is best to find someone local or broaden our horizon elsewhere? Thanks in advance for any and all suggestions in regards to this!

Basit Siddiqi · Answer

If you have a STR and you self-manage the proprety. You might want to see if you are eligible to treat the property as active instead of passive.This might result in a large tax refund.Best of luck!

Ashish Acharya · Answer

Hey @Aaron Mossburg,

Lots of great replies here! I’d definitely recommend jumping on a call and interviewing a few CPAs to see who aligns best with your goals and personality. Most firms these days are leaning toward virtual meetings, so you don’t necessarily need to limit yourself locally.

Since you’re already at 3 doors, you’ll want someone who’s more of an advisor, someone who can help you plan ahead, not just prep your taxes. You might even want a CPA who can handle it all, tax planning, bookkeeping guidance, and strategic advice, so you’re set up for growth and efficiency as your portfolio expands.

Here are 3 things I’d look for when interviewing CPAs for a real estate portfolio like yours:

• Real Estate Expertise: Experience with both long-term and short-term rentals, understanding of deductions, deferrals, and strategies to save on taxes.
• Proactive Guidance: Someone who actively looks for ways to optimize your portfolio and keeps you ahead of tax law changes.
• Communication Style: They should explain things clearly, answer your questions, and work in a way that fits your style, virtual meetings, email, calls, etc.

Once you narrow it down, you’ll have a much clearer picture of who can help you save the most and grow your portfolio efficiently.

William Thompson · Answer

That’s a smart question — and honestly, one of the best things you can do early in your investing journey.

The truth is, you don’t need to limit yourself to a local CPA — what matters most is finding someone who specializes in real estate taxation and understands how to structure your portfolio for maximum deductions and long-term strategy. Many of my clients are spread across different states, and with today’s tech, everything from cost segregation studies to entity planning can be handled virtually without sacrificing quality.

A great real estate CPA won’t just “do your taxes” — they’ll help you plan ahead, so you can take advantage of depreciation, 100% bonus write-offs (under the new 2025 bill), and passive/active loss rules that most general accountants miss.

If you’re already at three doors and thinking strategically about deferral, you’re at the perfect stage to start working with a tax strategist who can map out the next few years — not just this filing season.

Are you leaning more toward holding your properties long-term, or planning to add more STRs this year? That’ll help shape which strategies make the most sense for you.

Anthony Bonidie · Answer

Nice work building that portfolio, Aaron! Check if you can use the short-term rental loophole, just be sure your CPA’s familiar with it. I’d look for someone national that way you have more options!

Jason Malabute · Answer

You don’t necessarily need to find someone local. What’s more important is that your CPA has deep experience working with real estate investors — especially those who own both long-term and short-term rentals — and understands strategies like cost segregation, depreciation, and short-term rental material participation rules.  Make sure they are familiar with your state''s tax law.

Most CPAs who specialize in this niche work virtually anyway, so I’d recommend focusing on finding someone who can proactively help you plan year round and minimize taxes year over year rather than just file returns.

Josh L. · Answer

@Aaron Mossburg As others have mentioned, there are plenty of tax professionals in the tax forums and the Tax Pro Search who work nationwide and are well-versed in real estate tax.

Congrats on your portfolio.

Randall Tannen · Answer

@Aaron Mossburg

You'll find many on here who may fit the bill. In terms of local vs. virtual (and in some cases it might turn out to be the same thing), some have a strong preference for in person only. Otherwise, working virtually is just the same (if not much more convenient).

Tax Pro - here in Pittsburgh or elsewhere (virtual)?

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