538 tagged with "Tax"
Tax strategies, planning, and compliance for individuals and businesses
ISO vs. NSO Stock Options: A Startup Employee's Tax Guide to AMT, 83(b), Early Exercise, and the $100K Limit
A practical tax playbook for startup employees holding ISOs or NSOs — covering AMT exposure via Form 6251 line 2i, the 30-day Section 83(b) deadline, the two-year-and-one-year qualifying disposition rule, the $100,000 first-exercisable ISO cap, and the 1099-B cost basis error that causes double taxation.
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 1033 Involuntary Conversion: A Non-Farm Business Guide to Deferring Gain on Property Destroyed, Stolen, or Condemned
Section 1033 lets non-farm businesses defer gain on property that is destroyed, stolen, or condemned if the proceeds are reinvested in qualifying replacement property within 2, 3, or 4 years. This guide covers the election mechanics on Form 4797, the similar-or-related-in-service-or-use vs. like-kind tests, the carryover-basis recapture trap, and the bookkeeping needed to survive an IRS look-back.
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.
Section 277 and 501(c)(7): Member vs. Nonmember Income for Social Clubs
Section 501(c)(7) social clubs must keep nonmember income under 35% of gross receipts and nonmember facility use under 15%, while Section 277 quarantines member-side losses for nonexempt membership organizations. This guide walks through how the two rules interact, how to allocate UBTI expenses on Form 990-T, and how to structure a chart of accounts so the member/nonmember split survives an IRS examination.
Section 467 Rental Agreements: Stepped, Prepaid, and Deferred Rent Under the Tax Code's Anti-Abuse Rule
Section 467 forces accrual accounting and imputed interest on commercial leases over $250,000 with stepped, prepaid, or deferred rent — overriding cash-basis treatment, recharacterizing part of every rent payment as a deemed loan between landlord and tenant, and creating Schedule M-1 book-tax differences from ASC 842 straight-line rent.
The Self-Rental Rule Under Section 469: How the Grouping Election Defuses the Passive Loss Trap
Section 469's self-rental rule recharacterizes rent from your own building as active income while losses stay passive — a one-way street that traps small business owners. A timely grouping election under Reg. 1.469-4 defuses it; missing the first-return filing window usually means living with the asymmetry for good.
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.
Form 1120-H vs. Form 1120 for HOAs: The Section 528 Election, the 60/90 Tests, and Revenue Ruling 70-604, Explained
A practical guide for HOA boards, treasurers, and small-firm CPAs on the Section 528 election, the four Form 1120-H eligibility tests, the 30% flat rate trade-off versus Form 1120, and why every association should record an annual Revenue Ruling 70-604 vote.
IRS Office of Appeals and Audit Reconsideration: How Small Businesses Fight an Audit Without Going to Tax Court
A small business guide to resolving IRS audit disputes without litigation — the 30-day letter, Form 12203 Small Case Request, formal written protest, Fast Track Settlement, audit reconsideration, and the 90-day statutory notice of deficiency.
The Minister's Housing Allowance: Section 107, the SECA Trap, and the Retired-Pastor 403(b) Designation
Section 107 lets ordained ministers exclude designated housing costs from federal income tax, but the allowance is still added back for SECA and only an in-advance written designation survives audit. A practical guide to the three-part cap, Form 4361's irrevocable opt-out, and the 403(b) designation that keeps a retired pastor's distribution income-tax-free for life.