Form 1099-S Demystified: How the Right Closing-Day Certification Can Spare You a Surprise Tax Bill on Your Home Sale
Form 1099-S reports the gross sale price of a home, not the net, which routinely triggers IRS CP2000 notices for sellers whose gain is fully excluded under Section 121. This guide explains the Rev. Proc. 2007-12 certification that lets qualifying principal-residence sales bypass the form, the $250,000/$500,000 thresholds, the nonqualified use trap added in 2008, and how to defensibly report when the 1099-S cannot be skipped.
How the OBBBA's Tiered QSBS Exclusion Changes the Math for Founders, Employees, and Angels
The OBBBA raised the Section 1202 QSBS cap to $15 million, lifted the gross-asset ceiling to $75 million, and replaced the five-year cliff with a tiered 50/75/100 percent exclusion at three, four, and five years — but only for stock issued after July 4, 2025.
Section 1031 Boot Recognition: Cash Boot, Mortgage Boot, and Partial Deferral on Form 8824
A working guide to how the IRS computes boot in a Section 1031 exchange — cash boot, mortgage boot, the four netting rules, depreciation recapture at 25%, carryover basis, and Form 8824 reporting — with a worked example showing how $200K of fresh equity can wipe out $200K of mortgage boot.
Section 707(a)(2)(B) Disguised Sale Rules: How LLC Members Contribute Property and Take Cash Without Triggering a Taxable Sale
Section 707(a)(2)(B) recharacterizes paired property contributions and cash distributions to LLC members as taxable sales when they occur within two years. A walkthrough of the two-prong test, the rebuttable two-year presumption, the four regulatory exceptions, debt-financed distribution mechanics, and the Form 8275 disclosure that keeps partners out of audit trouble.
The 30-Day Decision That Can Save Founders Millions: A Plain-English Guide to the Section 83(b) Election
A Section 83(b) election lets founders and early employees pay ordinary income tax today on the full value of restricted stock instead of at each vest. Filed within 30 days on IRS Form 15620, it can convert millions of phantom ordinary income into long-term capital gain and start the QSBS holding clock on day one.
Form 1099-DA, Per-Wallet Cost Basis, and the Rev. Proc. 2024-28 Safe Harbor: A 2026 Crypto Tax Guide
Form 1099-DA introduces IRS broker reporting for digital asset sales beginning with 2025 transactions and adds cost-basis reporting for covered assets in 2026. Rev. Proc. 2024-28 simultaneously ends universal wallet accounting in favor of per-account allocation. This guide explains how investors and businesses reconcile 1099-DA against their own records, use the one-time safe harbor, and avoid paying capital gains tax twice.
Give It Now or Leave It Later? The Basis Trap That Quietly Costs Families Hundreds of Thousands in Capital Gains Tax
Lifetime gifts under IRC Section 1015 carry over the donor's basis, while inheritance under Section 1014 steps it up to fair market value at death — a difference that can shift a family's after-tax outcome by six figures on a single appreciated position under the 2026 $15 million federal exemption.
Section 1248 Deemed Dividend on CFC Stock Sales: A U.S. Shareholder's Guide to E&P, GILTI, and PTEP
Section 1248 recharacterizes part of a U.S. shareholder's gain on the sale of CFC stock as a dividend, capped by the corporation's earnings and profits and reduced by PTEP from GILTI and Subpart F inclusions. This guide explains who is affected, how the lookback works, why corporate sellers can prefer the recharacterization for Section 245A, and how to build a defensible work paper.
Section 302 Stock Redemptions: Sale vs. Dividend Treatment in Closely-Held C Corporations
A practical guide to Section 302 stock redemptions in closely-held C corporations — when a buyback gets capital gain treatment versus dividend treatment, how Section 318 family attribution disqualifies most family redemptions, and how the four 302(b) tests plus the 302(c)(2) waiver preserve sale treatment.
Direct Indexing for Tax-Loss Harvesting in 2026: The Loss Machine ETFs Cannot Build
A 2026 guide to direct indexing — how owning the 500 underlying stocks of an index in a separately managed account harvests $18,281 of losses per year on average versus $4,808 for ETF investors, why the §1091 wash-sale rule and Rev. Rul. 2008-5 IRA trap can destroy your tax alpha, the platforms (Frec, Wealthfront, Schwab, Vanguard, BlackRock Aperio) competing at 9–40 bps with $5K–$1M minimums, and the loss-exhaustion problem that limits the strategy to a 5–10 year shelf life.
Form 6252 and Installment Sales: A Working Guide to Section 453
A practical guide to Section 453 installment sales and Form 6252 — how the gross profit ratio defers capital gains across years, when depreciation recapture forces year-one recognition, how the Section 453A interest charge applies above the $5 million threshold, and when electing out beats deferral.
Form 6252 Installment Sales Under Section 453: Spreading Capital Gains and Avoiding the 453A Interest Charge
A practical walk-through of reporting installment sales on Form 6252 under IRC Section 453 — computing the gross profit percentage, why depreciation recapture is taxed in year one, the 453A interest charge on notes above the $5M aggregate threshold, the two-year related-party resale rule, and when electing out beats deferring gain.