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#tax-planning

Tax Planning

Strategic tax planning to minimize liability and maximize savings

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.

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.

Section 45F in 2026: How OBBBA Quadrupled the Employer-Provided Child Care Credit

Starting in 2026, the One Big Beautiful Bill Act expands Section 45F's Employer-Provided Child Care Credit from 25% to 40% (50% for businesses under $32M in average gross receipts) and lifts the annual cap from $150,000 to $500,000 ($600,000 for small businesses), with new explicit rules for intermediaries, pooled arrangements, backup care, and reserved-seat contracts.