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Tax
Tax strategies, planning, and compliance for individuals and businesses
Section 267 Explained: Related-Party Loss Disallowance and the Matching Rule
Section 267 disallows losses on sales between related parties and defers deductions on accrued payments to related cash-basis payees. A practical guide to who counts as related, how constructive ownership works, the 267(d) gain offset, the 2.5-month payment safe harbor, and the bookkeeping habits that keep family businesses and partnerships audit-ready.
Section 514 UDFI Demystified: How Nonprofits, Foundations, and Self-Directed IRAs Get Taxed on Borrowed-Money Investments
How Section 514 of the Internal Revenue Code taxes leveraged investments held by 501(c)(3) organizations, private foundations, and self-directed IRAs — including the debt/basis percentage calculation, Form 990-T mechanics, the 12-month look-back on sale, and the Section 514(c)(9) real estate exception for schools and pension trusts.
Section 988 Foreign Currency Transactions: A Tax Guide for Importers, Exporters, and Remote Workers
Section 988 of the Internal Revenue Code makes foreign-exchange gains and losses ordinary, not capital. Importers, exporters, and remote workers paid in euros or pounds get full ordinary-loss deductions with no $3,000 cap, a same-day election to convert forward-contract gains to capital, and a $200 per-transaction de minimis exception for personal travel currency.
Repair or Capitalize? A Plain-English Guide to the Section 263(a)-3 Tangible Property Rules for Small Businesses
How the IRS Section 263(a)-3 tangible property regulations decide what small businesses can deduct now versus capitalize over decades — with the three safe harbors ($2,500/$5,000 de minimis, the small taxpayer building rule, and routine maintenance), the BRA test, and the unit-of-property trap that drives most mistakes.
The 2026 W-4 Multiple Jobs Trap: How Two-Earner Households Stop Owing a Surprise Tax Bill Every April
When two spouses each fill out a default W-4, their employers withhold as if each job were the household's only income — causing systematic under-withholding. Step 2 of the 2026 W-4 closes that gap with three options: the checkbox, the Multiple Jobs Worksheet, and the IRS Tax Withholding Estimator.
Barter Transactions: How to Record Trades and Report Them to the IRS
Every barter trade creates taxable income equal to the fair market value of what you receive. Record it as a paired sale and expense through a barter clearing account, then report it on Schedule C—including 15.3% self-employment tax—and watch for Form 1099-B from barter exchanges.
Are Business Credit Card Rewards Taxable? How to Record Cash Back, Points, and Bonuses
For most businesses, credit card cash back and points are non-taxable rebates, not income—but a bonus with no spending requirement is taxable. Spending rewards also reduce your deductible expenses, so record them as a contra-expense to keep deductions accurate.
Collection Due Process Hearings: How a 30-Day Letter Stands Between Your Small Business and an IRS Bank Levy
A timely Form 12153 filed within 30 days of IRS Letter 3172 or LT11/L-1058 triggers a Collection Due Process hearing under IRC Sections 6320 and 6330 — suspending levy action, preserving Tax Court appeal rights, and giving small business owners a statutory chance to negotiate installment agreements, lien withdrawal, innocent spouse relief, or offers in compromise before the IRS drains the operating account.
The F Reorganization: How S Corporations Restructure Tax-Free Before a Sale
An F reorganization under IRC Section 368(a)(1)(F) lets an S corporation restructure tax-free into a holding-company/QSub form so a buyer gets an asset basis step-up at any ownership percentage and sellers can defer tax on rollover equity.
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.
Form 1099-R Box 7 Distribution Codes, Decoded
Box 7 of Form 1099-R holds a one- or two-character code that decides whether a retirement distribution is taxable, penalty-free, or hit with a 10% early-withdrawal penalty. This guide explains every numeric and letter code, including the new Code Y for qualified charitable distributions, and the coding errors that overcharge taxpayers.