Skip to main content
Tax Planning

Everything About Tax Planning

243 articles
Strategic tax planning to minimize liability and maximize savings

Section 6166 Estate Tax Deferral for Closely-Held Businesses: The 14-Year Installment Election in 2026

How executors of closely-held business estates use IRC Section 6166 to defer federal estate tax across 14 years at a 2% rate, with the 2026 inflation-adjusted $1.94M base, the 35% eligibility test, election mechanics, and the acceleration events that kill the deferral.

Section 754 Election: How Partnerships Use Inside Basis Step-Ups to Save Incoming Partners and Heirs From Phantom Gains

A Section 754 election lets a partnership adjust the inside basis of its assets when an interest transfers or property is distributed, preventing incoming partners and heirs from being taxed on appreciation that economically belonged to the seller. The election is permanent, covers both 743(b) and 734(b) adjustments, and matters most for real estate, family, and professional service partnerships.

Tax Planning During Divorce: QDROs, Post-TCJA Alimony, and Section 1041 Property Transfers

A practitioner's guide to the tax mechanics of divorce — how a QDRO splits a 401(k) penalty-free, why alimony in agreements executed after 2018 is no longer deductible, how Section 1041 carryover basis can turn a 50/50 settlement into an unequal one, and how the Section 121 home-sale exclusion survives when one spouse moves out.

401(k) Hardship Withdrawals and Plan Loans Under SECURE 2.0: When to Tap Retirement Funds Without Wrecking Your Future

A record 6% of 401(k) participants took a hardship withdrawal in 2025. This guide compares hardship withdrawals, plan loans, and SECURE 2.0 penalty-free distributions—with the actual tax math, deemed-distribution traps, and a decision framework for when to tap retirement funds.

529-to-Roth IRA Rollover: Move $35,000 of Unused College Savings Into Tax-Free Retirement

SECURE 2.0 lets the beneficiary of a 529 plan roll up to $35,000 of unused college savings into a Roth IRA tax-free and outside Roth income limits, provided the account is 15+ years old, contributions are 5+ years seasoned, and the beneficiary has earned income. This guide walks through the five federal tests, the state tax clawbacks that can erase the benefit, and a clean five-year execution plan.

The Accountable Plan: How S-Corp Owners Reimburse Themselves Tax-Free for Home Office, Mileage, and Travel

A working IRS-compliant accountable plan lets S-Corp owners reimburse home office, 72.5¢/mile mileage, internet, and travel tax-free—turning otherwise-lost expenses into deductible corporate spending. This guide covers the three §1.62-2 requirements, a worked $3,126 home office calculation, the five mistakes that get plans reclassified as wages, and the monthly bookkeeping rhythm that keeps it audit-proof.

The Connelly Trap: How a Unanimous Supreme Court Decision Broke Decades of Buy-Sell Agreements—and What Co-Owners Must Do Now

Connelly v. United States, decided unanimously on June 6, 2024, ruled that company-owned life insurance proceeds count toward a deceased shareholder's estate—adding $889,914 in federal estate tax for one Missouri family. This guide explains why redemption-funded buy-sell agreements now backfire and walks through five workable alternatives, including cross-purchase structures, insurance LLCs, and ILITs.

Donor-Advised Funds and the Charitable Bunching Strategy: Beating the 2026 Tax Floor with Concentrated Giving

The OBBBA's 0.5% AGI floor and 35% deduction cap take effect in the 2026 tax year, raising the cost of small annual gifts. Concentrating four years of donations into a single donor-advised fund contribution can add roughly $39,600 in total deductions for a $200,000-AGI couple while keeping the recipient charities on their normal schedule.

ESOP Section 1042 Rollover: How C-Corp Owners Can Sell to Employees and Defer (or Eliminate) Capital Gains Tax

Section 1042 of the IRC lets a C-corporation owner selling shares to an ESOP defer federal capital gains tax indefinitely — and potentially eliminate it through step-up at death. This guide covers the five qualifying conditions, what counts as Qualified Replacement Property, the floating-rate-note diversification strategy, and the trade-offs founders should weigh against a strategic sale.

Nonqualified Deferred Compensation: Section 409A, Rabbi Trusts, and the 20% Penalty Executives Need to Avoid

Section 409A lets companies defer executive pay above 401(k) limits, but a single misstep triggers immediate taxation on every vested dollar plus a 20% federal penalty and premium interest. Here is how NQDC plans, rabbi trusts, and the six permissible distribution triggers actually work.