For wealthy individuals, and non-grantor trusts and estates, we are going to have to learn how to deal with the new 2/37th limitation on claiming itemized deductions under the One Big Beautiful Bill.

The IRS has now provided the Final Regulations on when catch-up contributions must be made to a 401(k) account as a Roth (after-tax) contribution. Fortunately, there are several examples in these Final Regulations that help to explain when and how a plan participant must make Roth catch-up contributions to his/her 401(k) account and when and how changes in compensation are handled, either falling under this Roth contribution rule, or when a participant is no longer covered under the mandatory Roth contribution rule due to a decrease in compensation.

The One Big Beautiful Bill Act provides a new set of favorable rules for Qualified Opportunity Zone Investments, starting in 2027. However,  that also means that current Qualified Opportunity Zone investments will face a critical liquidity event at the end of 2026 when the gain deferral for those investments ends.

Charitable planning for the future will require more thought and less impulse if tax deductions are part of the motivation for a donor’s philanthropy. Perhaps even more tax law changes will appear over the next 18 months as performative politics enters the world of philanthropy.

The Spizzirri decision is a good reminder that the Tax Code provides strict conditions before a claim can be deducted from the gross estate when it pertains to family agreements or prenuptial agreements, that look more like testamentary arrangements, and as such ‘creative contract’ provisions in a prenuptial agreement will probably not produce a beneficial deductible debt of the decedent’s estate.

Choosing between a solo 401(k) plan and a Simplified Employee Plan, or SEP IRA,  depends upon the income and goals of the self-employed individual, along with how much flexibility is desired when making contributions to the retirement plan.

More small business owners are expected to qualify for the qualified business income (QBI) tax deduction if they itemize their income taxes with the OBBBA changes. This includes Airbnb owners. The challenge will be either for the Airbnb owner to qualify as a ‘trade-or-business’ but then he/she must expect to pay Social Security and Medicare taxes as a trade-off to claiming the QBI deduction, or the owner must elect to fall within the IRS’s safe harbor, which entails detailed record-keeping, logs, and documenting at least 250 hours a year devoted to the Airbnb activity.

Many courts seem to be reluctant to enforce a in terrorem, or no-contest, provision in a Trust or Will. While no-contest provisions are generally intended to prevent challenges to the validity of a trust instrument, all too often the no-contest provision is written very broadly with sweeping language that seeks to cover all post-mortem actions in the probate court.

Trump Accounts are a new opportunity to save for children. Making a Trump Account a ‘sort of’ traditional IRA, with some (but not all) IRA rules applicable will probably cause a lot of confusion when it comes to the tax consequences of contributing to a Trump Account and taking distributions from a Trump Account. The rhetorical question always will linger- is the hassle worth it? All I know is that I have typed the word Trump at least 60 times in this missive, so at least I’ve made at least one person we know very happy.

Special distribution rules apply when a spouse dies naming his/her surviving spouse as the IRA’s designated beneficiary. A surviving spouse has options, especially so after the SECURE 2.0 Act. Note a rollover election is irrevocable. These new rules may not make much difference if the surviving spouse is close to his/her required beginning date, but for younger surviving spouses, these changes can make a big difference in when and how much required minimum distributions will have to be taken.