Opportunity Zones 2.0: A 2026 Planning Guide for Real Estate Sponsors and Family Offices
The One Big Beautiful Bill Act made Qualified Opportunity Zones permanent and introduced rolling 5-year deferrals, decennial map redesignations starting July 1, 2026, a new rural fund class (QROF) with a 30% basis step-up at year 5, and $10,000-per-return reporting penalties. Here is the planning sequence for sponsors and family offices through the 2026–2027 window.
Section 1202 QSBS After the One Big Beautiful Bill Act: Tiered Holding Periods, the $15 Million Cap, and Trust Stacking
How the One Big Beautiful Bill Act rewrote Section 1202 QSBS — a tiered 50/75/100% gain exclusion at three, four, and five years; a $15 million per-issuer cap; a $75 million gross asset threshold at issuance; and non-grantor trust stacking that can lift a founder's combined exclusion well past the single-taxpayer limit.
Section 1202 QSBS Exclusion: A Founder's Guide to $15 Million in Tax-Free Gains
Section 1202 lets founders, early employees, and angel investors exclude up to $15 million of capital gains from federal tax. This guide covers the OBBBA changes, the five eligibility gates, the new 3/4/5-year tiered holding period, Section 1045 rollovers, and stacking strategies that multiply the per-issuer cap across family members and non-grantor trusts.
Section 736 Payments to Retiring or Deceased Partners: 736(a) vs. 736(b), Hot Assets, and the Goodwill Lever
Section 736 splits liquidating payments to a retiring partner into 736(b) property payments (capital gain, no firm deduction) and 736(a) income or guaranteed payments (ordinary income with self-employment tax, deductible by the firm). The service-partnership carve-out, Section 751 hot assets, and Section 754 election together determine whether six- or seven-figure tax dollars land on the retiree or the firm.
Form 1099-DIV Box 3: The Return-of-Capital Basis Trap for REIT, BDC, and MLP Investors
A practical walkthrough of Form 1099-DIV Box 3 nondividend distributions — how return-of-capital payments from REITs, BDCs, MLPs, and managed-distribution funds reduce your cost basis under IRC Section 301(c)(2), convert into immediate capital gain under 301(c)(3) once basis hits zero, and what records you need to keep so the IRS matching program never catches you short.
Section 1059 Extraordinary Dividend Basis Reduction: The Corporate Shareholder Trap That Turns Tax-Free Dividends Into Immediate Capital Gain
Section 1059 reduces a corporate shareholder's stock basis by the nontaxed portion of an extraordinary dividend — 5% threshold for preferred, 10% for common — when received within two years of acquisition, with excess immediately taxed as capital gain. This guide covers the thresholds, the 85-day and 365-day aggregation rules, the FMV election, the non-pro-rata redemption exceptions, and the lot-level bookkeeping that keeps corporate finance teams out of audit trouble.
When Capital Gain Becomes Ordinary Income: Section 1239 and the Family Business Trap
Section 1239 converts capital gain to ordinary income on sales of depreciable property between related parties — including a controlling owner and their own corporation, partnership, or trust. The constructive ownership rules under Section 267(c) make the more-than-50% threshold easier to cross than family business owners expect.
California Proposition 19 and the End of the Old Parent-Child Property Tax Bargain: A 2026 Guide for Heirs of California Real Estate
How California's Proposition 19 replaced Section 63.1 for parent-child transfers after February 16, 2021 — the family home and farm rules, the one-year occupancy requirement, the BOE-19-P and BOE-266 filings, the $1,044,586 value cap floor, and the step-up-basis trade-off that determines whether to gift during life or transfer at death.
Section 1041 and Divorce: A Guide to Property Transfers, Carryover Basis, and QDROs
Section 1041 lets spouses transfer property tax-free during and after divorce, but carryover basis, the six-year window, QDROs, ISO conversions, and post-TCJA alimony rules quietly reshape every settlement. A working guide to what must be fixed before the decree is signed.
Section 1235 Capital Gains Treatment for Patent Sales: How Inventors Convert Royalty Income Into Long-Term Capital Gain
Section 1235 lets individual inventors and qualifying early investors treat a patent sale as long-term capital gain — even without a one-year holding period — if they transfer all substantial rights. This guide explains who qualifies as a holder, why the rule survived the TCJA carve-out for self-created intangibles, and how to draft the transfer so the IRS sees a sale rather than a royalty license.
Form 1099-B Cost Basis: Reconciling Covered and Noncovered Securities on Form 8949
Brokers often report a wrong or zero cost basis on Form 1099-B, especially for RSUs and ESPP shares. This guide explains covered vs. noncovered securities, Box 1e and Box 5, and how Form 8949 adjustment code B corrects basis so you do not pay tax twice on the same income.
Form 1099-B Cost Basis Reconciliation: How to Avoid Paying Tax Twice on the Same Dollar
Form 1099-B Box 1e shows your broker's cost basis, but Box 5 determines whether the IRS sees it. A working guide to covered vs. noncovered securities, Form 8949 adjustment codes (B, W, Q, O, T), and the RSU/ESPP basis corrections that prevent double-taxation.