#tax-planning
Tax Planning
Strategic tax planning to minimize liability and maximize savings
Asset Sale vs Stock Sale: How M&A Deal Structure Decides Who Pays the Tax
An asset sale vs stock sale changes who pays tax, who carries liability, and how a deal closes. Compare 2026 tax math, successor liability doctrines, and the S-corp hybrid structures — Section 338(h)(10) and F-reorganizations — that now dominate mid-market deals.
Donor-Advised Funds vs Private Foundations: Choosing the Right Vehicle for Your Charitable Legacy
A 2026 comparison of donor-advised funds and private foundations covering AGI deduction limits, the 0.5% itemizer floor and 35% deduction cap from OBBBA, the 5% payout rule, self-dealing penalties, and why closely-held stock donated to a private foundation deducts at cost basis instead of fair market value.
Form 709 Gift Tax Return: When You Must File, the Annual Exclusion, and the $15M Lifetime Exemption
A practical guide to Form 709 for 2026 gifts — who must file, the $19,000 annual exclusion, the $15 million lifetime exemption, gift splitting rules, the adequate disclosure standard that starts the IRS three-year clock, and the medical and tuition payments that escape reporting entirely.
The Remote Worker's Multi-State Tax Survival Guide: Convenience Rules, Reciprocity, and How to Avoid Paying Twice
How state income tax really works for remote employees who cross state lines: the convenience-of-the-employer rule used by seven states (including New York), which reciprocity agreements eliminate double taxation, day-counting evidence auditors accept, and the bookkeeping habits that keep multi-state returns predictable.
Net Investment Income Tax (NIIT): A 3.8% Surtax Guide for High Earners and Investors
The 3.8% Net Investment Income Tax kicks in once MAGI crosses $200,000 single or $250,000 joint—thresholds frozen since 2013. This guide explains who pays NIIT, how Form 8960 calculates it, which income types count (interest, dividends, capital gains, passive rentals) and which don't (wages, IRA distributions, muni interest), plus planning levers to cut exposure.
Qualified Opportunity Zones in 2026: Capital Gains Deferral, Tax-Free Growth, and the OBBBA Reset
How Qualified Opportunity Funds defer capital gains, deliver tax-free appreciation after a 10-year hold, and what changes for new investments under OBBBA's permanent Opportunity Zones 2.0 rules starting January 2027.
SECURE Act 2.0 Decoded: The Retirement Rule Changes Reshaping 2026 for Savers and Small Businesses
SECURE 2.0 Act provisions taking effect in 2026 and 2027 — mandatory Roth catch-ups for earners over $145,000, RMD age pushed to 75 for those born after 1960, $35,000 lifetime 529-to-Roth rollovers, and up to $16,500 in small business retirement plan startup credits.
Step-Up in Basis at Death: The Estate Planning Strategy That Eliminates Capital Gains for Your Heirs
Section 1014 of the Internal Revenue Code resets an inherited asset's cost basis to its fair market value on the date of death, erasing the decedent's lifetime appreciation from the tax base — a provision the Joint Committee on Taxation estimates will cost the federal government $72.5 billion in 2026.
The 83(b) Election: A 30-Day Decision That Can Save Founders Six Figures in Taxes
A Section 83(b) election lets founders and early employees pay ordinary income tax on the grant-date value of restricted stock instead of on each vesting tranche, shifting future appreciation into long-term capital gains. The 30-day filing window is absolute and starts on the actual transfer date.
The Backdoor Roth IRA: A Step-by-Step Guide for High Earners in 2026
The Backdoor Roth IRA lets high earners contribute up to $7,500 a year to tax-free retirement growth by pairing a nondeductible traditional IRA contribution with a Roth conversion. Covers the five-step process, the pro-rata rule that derails most attempts, Form 8606 filing, and the recordkeeping that prevents being taxed twice.
Got a 1099-C? Why You Might Owe Nothing (and the Mistake That Costs People Thousands)
A 1099-C does not automatically mean a tax bill. This guide covers when canceled debt is taxable, the five Form 982 exclusions (bankruptcy, insolvency, qualified farm, real property business, principal residence), the 2026 expiration of the student loan and mortgage forgiveness exclusions, and the recordkeeping that proves insolvency to the IRS.
ESPP Tax Treatment: Qualified vs. Disqualifying Dispositions Explained
How qualified versus disqualifying dispositions change the tax bill on a Section 423 ESPP, with worked examples covering ordinary income, adjusted basis, Form 3922 cost-basis fixes, and a decision framework for when holding two years actually pays off.