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Tax
Tax strategies, planning, and compliance for individuals and businesses
Why Most NIL Collectives Aren't Real Charities (and Your Donation Isn't Deductible)
The IRS memorandum AM 2023-004 concluded that NIL collectives paying 80-100% of donations to athletes confer substantial private benefit and fail the operational test for 501(c)(3) status, so contributions to them are generally not tax-deductible.
Car Loan Interest Is Tax-Deductible Again: How the OBBBA $10,000 Above-the-Line Deduction Works for U.S.-Assembled Vehicles From 2025 Through 2028
The OBBBA restores a personal car-loan interest deduction—up to $10,000 per year, above-the-line, for tax years 2025 through 2028—on new U.S.-assembled vehicles financed after December 31, 2024. Mechanics covered include the MAGI phase-out starting at $100K single / $200K joint, Form 1098-VLI reporting beginning in 2026, mandatory VIN entry on Form 1040, and edge cases for refinances, trade-ins, leases, and co-signers.
The $40,000 SALT Cap: Should You Re-Itemize in 2026?
OBBBA raised the SALT deduction cap to $40,400 for 2026, but a 30-cent-per-dollar MAGI phase-down between $505,000 and $606,333 creates a roughly 45% effective marginal rate — the "SALT torpedo." Here is how to decide whether to re-itemize.
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.
Personal Use of a Company Vehicle: Imputed Income and W-2 Reporting
Personal use of a company car is taxable wages. This guide compares the three IRS valuation methods — Annual Lease Value, cents-per-mile (72.5¢ for 2026), and the $1.50 commuting rule — with worked examples and W-2 reporting steps.
Recording Sales Tax You Collect: A Liability, Not Revenue
Sales tax you collect belongs on the balance sheet as Sales Tax Payable, never on the income statement. Split each taxable sale into Sales Revenue and a tax liability, keep one account per jurisdiction, and reconcile so the payable zeroes out at filing time.
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 1341 and the Claim of Right Doctrine: Recovering Tax on Clawed-Back Bonuses
Section 1341 lets a taxpayer who repays more than $3,000 of previously taxed income recover the tax cost—via a deduction or a credit, whichever is lower—on the repayment-year return rather than by amending the old one.
The Section 1375 Sting Tax: How S Corporations Trigger the 21% Passive Income Tax and a Three-Year Termination Cliff
The Section 1375 sting tax hits an S corporation with a 21% corporate-level tax when it has C-corporation E&P and passive investment income above 25% of gross receipts; three consecutive years of that combination terminates the S election. This guide shows who is exposed, how excess net passive income is calculated, and how to defuse the trap.
Section 530 Safe Harbor: How to Avoid IRS Back Payroll Taxes on 1099 Workers
Section 530 of the Revenue Act of 1978 bars the IRS from collecting back employment taxes on misclassified contractors if a business met three tests—reporting consistency, substantive consistency, and a reasonable basis for treating the workers as 1099 contractors.
Section 6751(b) Supervisory Approval: The Procedural Defense That Can Erase IRS Penalties
Section 6751(b) requires a real IRS supervisor to personally approve penalties in writing before assessment. A working guide to using Chai, the Graev trilogy, and the December 2024 final regulations to defeat accuracy-related, fraud, and information-return penalties — which penalties qualify, what documents to demand, and how to raise the argument at Appeals before paying for Tax Court.
Section 707 Disguised Sale Rules: When a Partnership Contribution Becomes a Taxable Sale
A disguised sale under Section 707(a)(2)(B) collapses a partnership contribution and a related cash distribution into a taxable sale. Transfers within two years are presumed a sale; the deemed-sale fraction equals consideration received divided by property FMV.