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

Sam's List Editorial | 2026-06-06

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 vetted 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...