5 Portfolio Moves Worth Discussing With an Advisor Given 2026's Tax Environment

5 Portfolio Moves Worth Discussing With an Advisor Given 2026's Tax Environment

Portfolio tax planning in 2026 looks different than it did two years ago. The One Big Beautiful Bill Act (OBBBA) changed several provisions that interact directly with how your portfolio is structured — and most of those changes haven't made it into the average annual review yet.

None of this is a reason to make reactive moves. It is a reason to revisit conversations you may not have had recently.

These are five planning discussions worth having with a financial advisor before year end. Not prescriptive investment advice — but specific enough that you can walk into a meeting knowing what to ask about.

1. Roth Conversion Modeling With Updated QBI Phase-In Thresholds

The OBBBA raised the income phase-in thresholds for the Qualified Business Income deduction under IRC §199A, which affects how Roth conversions interact with overall tax liability for business owners.

Here's the situation worth discussing: for some self-employed individuals and S-corp owners, higher QBI phase-in thresholds create a band where additional ordinary income — like a Roth conversion — doesn't immediately trigger a marginal rate increase. That window varies significantly by income level, business structure, and filing status.

This is a calculation that requires your CPA and your financial advisor working from the same numbers. The output is a conversion ceiling — how many dollars you can convert this year before you cross into a higher effective rate. That ceiling may be larger in 2026 than it was in prior years for some business owners, and the right answer is a precise number, not a rough estimate.

If your advisor and your accountant haven't had a joint call about your Roth conversion strategy this year, that's the conversation to request.

2. Tax-Efficient Investing in 2026: Crypto Loss Harvesting With 1099-DA Data

If you have cryptocurrency exposure, the IRS's new per-account cost basis rules make tax-loss harvesting cleaner and more documentable than it was before.

Under the per-wallet rules now in effect, each wallet or exchange account is its own basis pool. That means you can identify specific lots at a loss within a given account, sell them to recognize the loss, and document the transaction clearly against the 1099-DA your exchange will issue.

The coordination piece: this works best when your financial advisor's year-end review and your crypto tax reporting are synchronized. A lot of advisors still treat crypto as a side issue handled at tax time. For investors with meaningful digital asset exposure, a coordinated review of crypto positions alongside traditional portfolio positions — looking at the full tax picture — is increasingly standard practice.

The wash sale rule does not apply to crypto under current law, so you can harvest the loss and immediately repurchase if you want to maintain the position. That's a legitimate planning tool, and per-wallet records make it easier to execute cleanly.

3. Capital Gains Planning: Qualified Opportunity Zones for Recognized Gains

If you've had a significant capital gain event this year — sale of a business, real estate disposition, large equity position sale — Qualified Opportunity Zone (QOZ) investments remain one of the few mechanisms available to defer gain recognition.

Under IRC §1400Z-2, investing recognized capital gains into a Qualified Opportunity Fund within 180 days defers the gain until the investment is sold or December 31, 2026 — whichever comes first. Investments held for at least 10 years also receive a step-up in basis on the appreciation generated within the fund.

Note the current-year timing constraint: gains deferred into a QOZ must now be recognized by the end of 2026 under current rules. Verify the precise current deadline and applicable rules with your advisor at the time of the conversation — the regulatory landscape here warrants confirmation before acting.

QOZ investments carry real investment risk. They're not appropriate for everyone. But for a client who realized a $500,000+ gain and has not yet acted on it, the tax deferral mechanics are substantial enough to warrant the conversation before the year closes.

4. Asset Location Strategy After the Permanent QBI Extension

The OBBBA made the IRC §199A QBI deduction permanent — it no longer expires after 2025. That's a meaningful change for business owners who structured assets with a short planning horizon in mind.

Some clients held appreciating assets inside S-corps or pass-through entities specifically to benefit from the QBI deduction under assumptions about temporary law. Now that the deduction is permanent, the holding structure question has a longer time horizon.

This doesn't mean restructuring is automatically the right move — transaction costs, embedded gains, and entity change mechanics all matter. But if your asset location strategy was built around a QBI deduction that was supposed to expire, it's worth a review given that it won't. The right question for your advisor: given permanent QBI, does my current entity structure for holding appreciating assets still make sense over a 10+ year horizon?

That's a question that requires a CPA and a financial advisor in the same conversation. If that review hasn't happened since the OBBBA passed, it belongs on the agenda.

5. Treasury and I-Bond Allocation for High-Income Clients in High-Tax States

This one is less dramatic but consistently overlooked: Treasury interest is exempt from state and local income tax. Federal interest income (bonds, CDs, money market funds holding Treasuries) is taxed at the federal level but not at the state level.

For a high-income client in California, New York, or New Jersey — states with 9–13% income tax rates — the after-tax yield on a Treasury held to maturity is meaningfully higher than the nominal yield on a comparable corporate bond or CD with equivalent federal rates.

The math: a $500,000 Treasury allocation yielding 4.5% generates $22,500 in interest. For a California resident in the top 13.3% bracket, holding that same interest in a CD instead of a Treasury costs roughly $3,000 a year in state tax. Actual savings depend on your yield, bracket, and state — but the structural advantage is the same. That's an asset location conversation, not a market timing call.

I-bonds add a wrinkle: the fixed rate component and the inflation adjustment both matter, and the annual purchase limit ($10,000 per person per year directly) limits their use as a primary fixed income strategy. But for clients who haven't revisited their fixed income allocation since rates moved, the conversation is worth having.

Have These Conversations With a Reviewed Advisor

None of these are decisions to make based on a blog post. They require real numbers, your specific tax situation, and an advisor who understands how the pieces interact.

Every move above also carries trade-offs — conversion taxes due now, QOZ investment risk, transaction costs on restructuring — which is exactly why the conversation matters more than the move itself.

Calculated Wealth works with investors, pre-retirees, and high-income earners on exactly this kind of coordinated tax-aware planning. Read their client reviews on Sam's List before you book the call: Calculated Wealth on Sam's List.

Sam's List is where you find financial advisors who've been reviewed by real clients — so you walk into that first meeting already knowing who you're talking to.