470 tagged with "Tax Planning"
Strategic tax planning to minimize liability and maximize savings
The Self-Rental Rule: Why Your Building Rents Are Nonpassive but Your Losses Stay Passive
Reg. 1.469-2(f)(6) recharacterizes net rental income from property you rent to your own active business as nonpassive while leaving rental losses passive. This guide explains the asymmetry, walks through a dentist example with a $200,000 cost segregation deduction, and shows how the Reg. 1.469-4 grouping election can collapse the rule.
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.
From Cash to Accrual Without a Tax Shock: Form 3115, Section 481(a), and the De Minimis Safe Harbor
A small-business guide to the forced cash-to-accrual switch: how Form 3115 works, how the Section 481(a) catch-up is calculated and spread over four years, and why the de minimis safe harbor is an annual election rather than a method change.
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.
F-Reorganization Under Section 368(a)(1)(F): The Pre-Closing Restructuring PE Buyers Use to Buy S Corporations
A practical walkthrough of the Section 368(a)(1)(F) reorganization — the six regulatory requirements, the six-step Rev. Rul. 2008-18 choreography, why PE buyers prefer it to a 338(h)(10) election, and how it preserves the operating EIN while giving the buyer asset-basis step-up and the seller tax-deferred rollover equity.
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.
The 2026 Form W-4 Multiple Jobs Worksheet: How Two-Earner Couples and Side-Hustlers Sidestep an April Tax Surprise
A plain-English walkthrough of Form W-4 Step 2(a), 2(b), and 2(c) for two-earner households and side-hustlers — including the higher-paying-job rule, side-hustle income on Step 4(a), and the 90%/100%/110% safe-harbor numbers that prevent an April tax bill or penalty.
The Interest-Free Loan That Isn't: How Section 7872 Imputes Interest on Family and Shareholder Loans
A below-market loan triggers Section 7872, which treats forgone interest as taxable income to the lender even when no cash changes hands. This guide covers the $10,000 and $100,000 de minimis exceptions, the gift tax connection, and how charging the AFR avoids the whole problem.
The IRA Once-Per-Year Rollover Rule: One 60-Day Rollover and the Trustee-to-Trustee Workaround
You get only one IRA-to-IRA 60-day rollover per rolling 12-month period, counting all your IRAs as one account — a limit the 2014 Bobrow Tax Court case made aggregate. Trustee-to-trustee transfers are exempt and unlimited.
MLP K-1 Tax Issues for Individual Investors: UBTI, Section 751 Recapture, and Multi-State Filings
A Master Limited Partnership pays cash quarterly but issues a Schedule K-1, not a 1099. Most distributions reduce your cost basis instead of being taxed, holding units in an IRA can trigger UBTI and a Form 990-T once income exceeds $1,000, and selling converts depreciation into ordinary income under Section 751 — taxed up to 37%.
MLP K-1 Tax Issues: UBTI, Section 751, and Multi-State Filings for Individual Investors
How individual MLP investors actually owe tax — UBTI on IRA-held units crosses the $1,000 Form 990-T threshold faster than expected, Section 751 reclassifies part of any sale gain as ordinary income, and the K-1's state schedule can force nonresident filings in operating states. Includes practical thresholds and basis-tracking rules.