Each page below walks through one strategy: how it works, the court case that tested it, and the documentation that decided the outcome. Every fact comes from the public opinion.
An accountable plan lets a business reimburse owner and employee expenses tax free under Treasury Regulation 1.62-2. The three requirements, what a defensible setup looks like, and the fraud case that shows what the absence of one looks like.
Read the strategy → Tax strategyThe Augusta rule lets a homeowner rent a residence to a business for up to 14 days a year and exclude the rent from income under Section 280A(g). How the valid version works, and what the Tax Court did in Sinopoli when the documentation was missing.
Read the strategy → Tax strategyPutting your kids on payroll is legitimate when the work is real. How the deduction works, when wages to a child under 18 escape Social Security and Medicare taxes and when they do not, and the records that make family payroll hold.
Read the strategy → Tax strategyA health savings account is deductible going in, grows untaxed, and comes out untaxed for qualified medical costs. How the triple advantage works, the high deductible plan eligibility rules that gate it, and the traps that undo contributions.
Read the strategy → Tax strategyHow a self employed owner contributes to a Solo 401(k) as both employee and employer, why the stack reaches far beyond an IRA, and the limits, deadlines, and eligibility rules that decide whether it works.
Read the strategy → Tax strategyAn S corporation owner must take a reasonable salary before profit distributions. What reasonable compensation means, how the IRS and the courts set the number, and three cases, Watson, McAlary, and Fleischer, where the record decided.
Read the strategy →What real estate professional status requires, the 750 hour and majority of time tests, material participation, and Mirch v. Commissioner, where a reconstructed time log cost three years of losses.
Read the strategy → Tax strategyWhy a rental with an average guest stay of seven days or less is not passive under Section 469, how material participation makes STR losses offset other income without real estate professional status, and what the hours log has to look like.
Read the strategy →How bunching several years of charitable gifts into one tax year makes itemizing pay, how a donor advised fund fits, and why the contemporaneous written acknowledgment decides whether the deduction survives.
Read the strategy → Tax strategyRealizing losses in taxable accounts offsets capital gains and a limited amount of ordinary income, with the rest carrying forward. How tax loss harvesting works, and the wash sale traps across IRAs, spouses, and reinvestment that quietly void it.
Read the strategy →In every case these pages cover, the strategy itself was legal and often ordinary. What failed was the implementation: the minutes never taken, the log built after the fact, the books that said something different from the return. If you want a written read on where your own setup stands, that is what the free Tax Position Review is for.
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