How are you all approaching tax strategy as your portfolio grows?

Question

Hey BP community,I’ve been working on scaling a small real estate portfolio with a couple of partners. As we move from simple buy-and-holds into more BRRRR-type deals, taxes and structuring are starting to feel more complex than when we first started.

I’m curious how others here handle it—do you stick with a general CPA, or have you found value in working with someone who really specializes in real estate tax strategy?

Would love to hear what’s worked (or not worked) for you all. I think it could help a lot of folks here who are trying to make the leap from a few properties to a more systematic business.

Ashish Acharya · Answer

Great points from everyone above and as Jason mentioned, tax laws are constantly changing, and from my experience, we’ve worked with many investors who came from other CPAs that didn’t fully grasp the nuances of real estate taxes. Sometimes important items get missed, such as cost segregation studies not being applied correctly or deductions being miscategorized, which can result in thousands of dollars being saved or lost.

That’s why it’s always important to make sure the professionals you work with share your goals and understand your strategy. Especially when you’re investing in real estate and spending money on professional services, you want a CPA (or advisor) who has the right background and experience (ideally someone who has done it themselves and truly understands the ins and outs of real estate investing).

Planning matters, but so do organized books and proper preparation. Real estate taxes can be complex, but a specialized CPA not only makes them easier to navigate, but they can also help you grow and scale while constantly educating you along the way.

Robert Norris Jr · Answer

@William Whitley - Do you have any recommendations for real estate focused professionals that provide tax prep and/or tax advisory services? I'm in middle TN but have properties in TN, NC, and under contract in AR.

William Whitley · Answer

@Robert Norris Jr, we should talk. I have some potential contacts for you. If you send me a message from my website, we can schedule a call. You can find my website under my profile. I can simply provide you some contact information and answer any questions you have.

William Thompson · Answer

Robert, I am a CPA who does exactly what you are looking for. My office is virtual and I work with RE investors all over the country. By the way, I am a RE investor who build a portfolio of 48 individual properties. I would be happy to help you.

William Whitley · Answer

A general CPA should be able to handle the tax compliance side of real estate investing, but there’s definitely added value in working with a CPA who specializes in real estate. Real estate has its own set of nuances such as depreciation, passive activity rules, cost segregation, entity structuring, that a specialist is going to be more fluent in.

For my part, I don’t provide tax prep or tax advisory. I focus on bookkeeping and financial consulting specifically for real estate investors. My role is more about helping clients track performance, analyze cash flow, and identify financial indicators that matter to their business. Then, when they also work with a CPA who specializes in real estate, the two perspectives complement each other — strong financial records and analysis on one side, specialized tax strategy on the other.

Jason Malabute · Answer

Great question, William. Once your portfolio starts moving beyond a couple of buy-and-holds into BRRRRs or more complex structures, taxes and compliance really do get trickier. In my experience, it’s less about whether you can keep up with it yourself and more about whether you’re confident you’re staying ahead of all the moving parts.

Tax laws—especially around real estate deductions, depreciation, passive activity rules, and elections like PTET—change almost every year. That’s why I’ve found it valuable to work with someone who specializes in real estate tax strategy rather than a generalist CPA. A specialist can help you not just file correctly, but also plan proactively—whether that’s structuring entities, timing capital improvements, or optimizing depreciation schedules.

In short: the bigger the portfolio, the more leverage you get from someone who lives and breathes real estate tax.

Benjamin Louie · Answer

@William Thompson

Great question, William. This is one of those “good problems to have” as the portfolio grows. 😅

From my experience, once you start doing BRRRRs and scaling past a couple of rentals, a general CPA can only take you so far. They’ll keep you compliant, sure, but they usually won’t proactively suggest strategies that save you money long-term.

When I switched to someone who really understood real estate, it was a game-changer, stuff like cost segregation, entity structuring, and knowing how to use depreciation the right way. Even just having them run “what if” scenarios before pulling the trigger on a deal saved me from headaches.

So I’d say if you’re serious about growing this into more of a business, finding a tax pro who lives and breathes real estate is worth it.

How are you all approaching tax strategy as your portfolio grows?

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