How to Talk to Your CPA About the OBBBA: Questions Every Investor Should Be Asking
The One Big Beautiful Bill Act (OBBBA) introduced sweeping changes across tax policy, real estate incentives, and wealth strategy.
But here’s the hard truth: most CPAs haven’t read the full text.
Some haven’t even read the summary.
And if you’re waiting until next March to hear what changed, you’re leaving opportunity—and money—on the table.
Here are the exact questions I recommend every investor, operator, or high-income earner ask their CPA now, while there’s still time to act on this year’s strategy.
1. How Will Bonus Depreciation Apply to My Portfolio This Year?
The return of 100% bonus depreciation is a game-changer—but only if:
You own qualifying assets
You plan to run cost segregation studies
You can actually use the losses
Ask your CPA to model out your projected K-1 losses, carryovers, and any active/passive limitations based on your 2025 income mix.
2. Do I Qualify for the SALT Cap Workaround Through PTET?
If you live in a high-tax state, your pass-through entity (LLC or S-Corp) may be able to pay your state taxes as a business expense, fully deductible at the federal level.
Ask:
Did we elect PTET this year?
Are we filing it correctly for federal deduction treatment?
Should I restructure to take advantage of this?
3. Can I Use Opportunity Zones for My Upcoming Gains?
Opportunity Zones were made permanent under OBBBA—with new zones coming in 2027 and basis step-ups as high as 30% in rural areas.
If you’re planning a business sale, real estate flip, or crypto liquidation, ask:
Can we time this gain to align with OZ eligibility?
Do I need to set up a QOF?
Can we pair this with trust or family office planning?
4. Are We Structured to Use the New Estate Tax Exemption?
The new exemption is $15M per person—$30M per couple—with no sunset clause.
That doesn’t mean you can stop planning. It means you can simplify, or optimize even further.
Ask:
Do our trusts and LLCs still serve us under the new rules?
Are our assets titled correctly for step-up planning?
Do we need a liquidity event modeled into our estate plan?
5. Are We Taking Advantage of Overtime or Tip Income Deductions?
These apply to your household income if you or your spouse have W-2 income with overtime or tips.
They may also affect:
Your tenants' ability to pay rent
The cash flow in businesses you invest in
Ask:
Can we deduct any portion of our household’s W-2 income under these provisions?
Should we update income assumptions in our real estate underwriting?
6. Do We Need to Make Any Entity or Filing Changes Before Year-End?
With so many changes now locked in through 2028, this is the time to align your entity structure, election status, and investment strategy with the updated rules.
Ask:
Are there elections or conversions we should file this year?
Are we maximizing S-Corp vs. partnership treatment?
Should we group certain businesses or investments?
Final Thought
I’ve been on both sides—CFO of a private equity fund, and now running a real estate-focused CPA firm. I can tell you: if you’re not asking the right questions, you’re already behind.
Your CPA might be great at filing. That’s not the same as planning.
The OBBBA gives you the tools. These questions make sure you’re actually using them.
