Charitable Remainder Trust (CRUT vs CRAT): Tax-Free Asset Sales and Lifetime Income
How a Charitable Remainder Trust lets you sell appreciated assets without capital gains tax, take an immediate income tax deduction, collect lifetime income, and pass the remainder to charity—plus the math comparing CRUT, CRAT, NIMCRUT, and Flip CRUT structures under the May 2026 5.0% Section 7520 rate.
Form 4797 Demystified: How Depreciation Recapture and Section 1231 Decide Whether Your Business Sale Is Ordinary or Capital
Form 4797 governs every business property sale outside Schedule D and decides whether your gain is ordinary or capital. This guide walks through Section 1245 and 1250 recapture, the Section 1231 five-year lookback rule, the 25% unrecaptured Section 1250 gain rate, and seven mistakes that trigger CP2000 notices.
Kiddie Tax Form 8615: How Investment Income for Children Under 24 Is Taxed at Parent Rates
How the federal kiddie tax pulls a child's unearned income above $2,700 in 2026 onto the parent's marginal rate via Form 8615. Mechanics, UTMA/UGMA pitfalls, full-time-student rules through age 23, and planning strategies using 529 plans, Roth IRAs, and gain timing.
Net Unrealized Appreciation: The 401(k) Tax Strategy That Saves Six Figures
The Net Unrealized Appreciation election lets retirees pay long-term capital gains rates on employer stock distributed from a 401(k) instead of ordinary income, often saving more than $144,000 on a $1 million position. Covers eligibility under IRC 402(e)(4), the lump-sum distribution rule, and the most common mistakes that destroy the strategy.
Reverse 1031 Exchange: How to Buy Your Replacement Property Before Selling the Old One
A reverse 1031 exchange lets a real estate investor close on a replacement property before selling the relinquished one by parking title with an Exchange Accommodation Titleholder under Revenue Procedure 2000-37's safe harbor. The taxpayer must identify the relinquished property within 45 days and complete the swap within 180 days, with no extensions. EAT fees typically run $5,000 to $15,000 above a forward exchange, so the deferred gain needs to be large enough to justify the cost.
Section 121 Home Sale Exclusion: How Homeowners Can Skip Up to $500,000 in Capital Gains Taxes
How Section 121 lets U.S. homeowners exclude up to $250,000 ($500,000 for joint filers) of capital gains on a primary home sale — covering the 24-month ownership and use tests, the two-year frequency rule, partial exclusions, depreciation recapture, and the nonqualified-use allocation.
Tax Loss Harvesting: The Year-Round Strategy That Can Save You Thousands in Capital Gains Taxes
Year-round tax loss harvesting can add 0.5%–1.5% in annual after-tax returns to a taxable portfolio. This guide explains the IRS netting order, the wash sale rule across taxable and IRA accounts, and a practical framework for harvesting short-term losses without losing the deduction.
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.
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.
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.