Have I outgrow my CPA?

Question

Have I Outgrown My CPA? Looking for Advice / Referrals

I’ve been with the same accounting firm for roughly 15 years, and they’ve been with me through a lot of growth. That said, I’m starting to wonder if my needs have evolved beyond what the relationship is currently providing.

Today I have a primary operating business along with a growing real estate portfolio of approximately 16 doors across multiple properties. My concern isn’t necessarily tax preparation—it’s the lack of proactive tax planning and real estate-specific guidance.

We typically have a tax-planning meeting toward the end of the year, but I’m increasingly feeling that November is too late to be making some of the decisions that should have been discussed throughout the year. I’d like more proactive guidance around things such as timing capital improvements and purchases, depreciation strategies, entity structure, financing decisions, and generally looking ahead rather than reacting after the fact.

At the same time, the accounting fees have increased substantially, and I’m questioning whether the level of strategy and advisory support I’m receiving justifies the cost.

For those of you who have built larger real estate portfolios:

• Have you ever reached a point where you felt you had outgrown your CPA or accounting firm?
• What did you look for when making a change?
• Did you move to a real-estate-focused CPA, a larger firm, or some type of tax advisory relationship?
• How frequently are you meeting with your CPA for proactive planning?
• And if anyone has a CPA or tax strategist they highly recommend for someone with both an operating business and a meaningful real estate portfolio, I’d appreciate referrals.

I’m not looking for the cheapest option. I’m looking for the right advisor who can be proactive, strategic, and grow with me.

Thanks in advance for any insight.

Aaron Zimmerman · Answer

Greg - I'd say this is fairly common in one way or another. Relationships sometimes don't last because one party outgrows the other party.

At this point, I'd probably recommend quarterly check ins as opposed to once a year. There's likely a lot you could do on the business side and also on the real estate side.

Christopher Tile · Answer

@Greg Heden

Agree with both @Michael Plaks and @Aaron Zimmerman.

Sometimes investors hang on with their CPA a little too long and make the switch too late.  Usually right after something in prior returns gets discovered or a lack of ongoing strategy. What you're describing is very common... and actually a good chunk of our new client conversations starts exactly this way. The prospective client will start building out a portfolio, ask questions to their existing CPA, and realize there's a gap in strategy/planning.

The fact that you're asking now (before something forces the issue) puts you ahead of most people in this position.

I suggest you start taking intro calls with a few investor-focused CPAs/EAs, including several who are active on this forum. Most will do a free consult. Use those calls to review their services and get specific. Ask how often they proactively reach out (not just at year-end), how they handle entity structure and depreciation planning across a growing portfolio, and whether they've worked with clients who have both an operating business and 15+ doors. Most have, since business planning and tax advantaged real estate investing often go together.

Michael Eskenasy · Answer

I don’t think the question is whether you’ve outgrown your CPA.

I think you’ve outgrown the service model you’re buying from them.

At 16 doors plus an operating business, November is too late for most of the decisions that actually matter. By then the acquisition happened, the financing was chosen, the improvement was made, the entity was used, and the money already moved.

The tax return is just documenting decisions that were made months earlier.

What I’d want at your stage is someone involved before the decision — not someone explaining the tax consequences afterward.

Before leaving a 15-year relationship, though, I’d give the current firm one clean opportunity. Tell them exactly what you need:

“I don’t need more meetings. I need someone helping me make tax-sensitive decisions throughout the year.”

Then ask what that engagement would actually look like.

Who calls whom?What triggers a review?Do acquisitions, sales, refinances and major CapEx automatically get discussed beforehand?Who is looking across the business and real estate together instead of treating them as separate tax returns?

If they can build that relationship, staying may be easier than starting over.

If they can’t, then yes — I’d shop.

But I’d interview for process, not for whoever uses the phrase “proactive tax planning” the most.

The right advisor should be able to tell you exactly how they would have interacted with you differently during the last 12 months.

That answer will tell you more than the size of the firm, meeting frequency or fee.

Kristine Nguyen · Answer

Hi Greg — with an operating business and a portfolio your size, I’d expect tax planning to happen throughout the year, not just in November. The least is quarterly planning, plus checking in with your CPA before major real estate transactions - especially acquisitions, sales, cash-out refinance and significant renovations. These events can create tax saving-planning opportunities that are much easier to evaluate before the transaction is completed.

When choosing a CPA, I’d look for someone who:

• - Works regularly with real estate investors.
• - Understands how your business and rental portfolio interact for tax purposes.
• - Is proactive about cost segregation/depreciation, passive activity rules, acquisitions and dispositions, and entity considerations.
• - Evaluates whether a strategy will actually benefit your specific tax situation.

Happy to be a resource!

Ashish Acharya · Answer

Greg, at this stage I’d expect the CPA relationship to look very different from what it did when the business and portfolio were smaller.

I’d want planning happening throughout the year, not mainly in November. Capital improvements, acquisitions, financing, retirement planning, depreciation, and business decisions are much easier to optimize before the transaction or tax year is nearly over.

Your CPA should also be helping you build a solid entity structure across the operating business and real estate portfolio. That does not necessarily mean creating more LLCs. It means understanding what each entity is doing, how it is taxed, where the properties should sit, how money moves between entities, and whether the structure still makes sense as you grow.

With an established portfolio, I’d also go back and review the older properties for cost segregation opportunities rather than only thinking about cost seg on the next acquisition. If a study was never performed, there may still be an opportunity to accelerate depreciation, potentially through an accounting-method change depending on the facts. The important part is doing the analysis first to determine whether the resulting losses actually improve your tax position or simply create more suspended passive losses.

I’d also want regular review of partial dispositions, major capital improvements, passive-loss limitations, and whether the operating business entity and compensation structure still make sense.

Higher fees alone would not make me leave a CPA. But if the strategy and advisory relationship have not grown with the complexity of the business and portfolio, that is a reasonable sign that you may need a more proactive, real-estate-focused team.

Happy to connect!

Sean Culloden · Answer

I think listing what has been proposed in those November meetings as far as proactive tax planning would make the decision to switch or retain your CPA evident. If the concept of REPS or cost segregation has never been mentioned you have your evidence. I understand your fees have increased in the last 15 years but that is not in itself alarming. I think many investors have been paying for solely tax prep for a long time or have been dealing with tax pros that focus solely on tax prep and are understandably frustrated they have not received valuable proactive planning. I would determine first if you are working with a tax firm that is capable of providing quality proactive planning or if you are working with a firm focused solely on tax prep. Proactive planning will be significantly more expensive than tax prep and should be discussed as a service provided outside of tax prep.I think the industry has done a bad job of making the difference between prep and planning clear with the exception of TikTok "tax strategists" who do not represent the vast majority of tax firms (thankfully). Find someone who is experienced and focused on providing planning first and knows how to take that planning and translate it to a tax return, not the other way around.

Michael Plaks · Answer

Completely agree with @Jason Malabute that many (if not most of the) times "proactive tax strategy" is nothing but a marketing slogan/ploy.

Which, ironically, also applies to the quarterly meetings idea. It is not how often meetings happen, it is what is the practical outcome of these meetings. Anybody who ever worked in corporate knows what I mean.

Michael Plaks · Answer

@Greg Heden

As someone who has operated an investor-only tax firm for 30 years, I wrote multiple posts discussing working with CPAs. You might find these posts helpful, I linked them here.One point though. A lot of people talk/brag about proactive tax strategies, it's fashionable. Very few actually deliver. Frequency of meetings does not necessarily translate into tangible improvement. Meetings need to provide actual value, not just an impression of "proactive planning." Happy to connect.https://www.biggerpockets.com/forums/51/topics/1088325-expla...https://www.biggerpockets.com/forums/51/topics/1222774-expla...https://www.biggerpockets.com/forums/51/topics/998718-explai...

Bill Hampton · Answer

@Greg Heden

I recommend finding an accountant who specializes in business taxation, real estate taxation, cost segregations, bonus depreciation, and is proactive instead of reactive when providing advice.

Working remotely with your accountant will expand your options. The best person for the job may not be local.

I would also recommend looking for an accountant who will work with you throughout the year. You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year. You should be meeting at least quarterly.

Happy to answer any questions. Good luck.

Jason Malabute · Answer

What you're describing is common, and the November meeting is the tell. By then it's a review, not planning, because most of the decisions that actually moved the needle already happened. Shifting to a quarterly rhythm often fixes more than switching firms does, since it gives you a chance to talk through a purchase, an improvement, or a financing decision while you can still change the outcome. I'd also be a little skeptical of anyone who leads with proactive tax strategy as a slogan, because it's a phrase that gets used a lot and doesn't mean much on its own. Before you commit to anyone, ask what they'd do differently with an operating business and sixteen doors specifically, and see whether the answer is concrete or just marketing. The other thing worth knowing is that most investors hang on longer than they should and only make the move after something ugly surfaces in a prior return, so if the relationship already feels thin you're not jumping early. The right fit depends a lot on how your entities and portfolio are structured, so it's worth having two or three conversations before you decide.

Have I outgrow my CPA?

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