Have You Outgrown Your CPA?

Question

Here’s a question I think more real estate investors should ask themselves:

Is your CPA helping you plan, or just helping you file?

There’s nothing wrong with having someone prepare your return.

But once your portfolio starts growing, the questions get bigger.

Should you buy this property?Should you do a cost seg?Can you actually use the losses?What happens if you refinance or sell?Does your entity structure still make sense?

Those conversations need to happen before the transaction, not after.

I’ve seen investors with multiple properties still approaching taxes like they did when they owned their first rental.

So I’m curious:

What do you expect from your CPA besides preparing your tax return?

I’d love to hear what other investors think.

And if you’re not sure whether your current tax strategy is keeping up with your portfolio, feel free to reach out. I’m happy to help clarify things.

Aaron Zimmerman · Answer

It  depends what type of relationship you're paying for

Igor Ganapolsky · Answer

William, great question. I'll give you one specific scenario where the "file vs. plan" distinction becomes critical: tax deed auction acquisitions.When you buy a property at a county tax deed auction, you're typically acquiring it at 50-70% of assessed value. That creates a completely different tax picture than a retail purchase — and most CPAs who haven't dealt with auction acquisitions miss it entirely.The cost seg question you raised becomes much more interesting when your depreciable basis is $160K on a property worth $250K at market. The land-to-improvement allocation, the depreciation schedule, the bonus depreciation applicability — all of those calculations start from a basis that's 30-50% below what a traditional buyer would have. That means your depreciation deductions are lower in absolute terms, but your cash-on-cash return is dramatically higher because your actual invested capital is so much less.Then there's the question of whether you can actually use the losses — which depends on whether you qualify as a real estate professional, whether the property is held in the right entity, and whether your CPA understands that tax deed acquisitions create different holding period and capital gains treatment than a typical MLS purchase.I'm working on Broward County (FL) Auction #113 in October — 16 properties at 50-70% of assessed value. The investors I'm talking to about bidding need exactly the kind of pre-transaction tax planning you're describing. The acquisition basis creates opportunities (lower depreciation but much higher cash-on-cash) and traps (basis allocation, potential quiet title costs, entity structure for auction vs. post-auction holding) that a filing-only CPA would never flag.The deeper point: when your acquisition creates instant equity through discount purchase, the tax strategy needs to be designed around that specific basis — not around a retail purchase model that assumes you paid market price. That's a planning conversation, not a filing conversation.