#tax-planning
Tax Planning
Strategic tax planning to minimize liability and maximize savings
HSA vs FSA vs HRA in 2026: The Practical Playbook for Picking, Stacking, and Not Forfeiting Your Health Dollars
A 2026 walk-through of HSA, FSA, and HRA rules with the new contribution limits, the limited-purpose FSA stack that adds up to $7,800 of pre-tax room, and how small employers can use ICHRA and QSEHRA to compete with corporate benefits.
The Mega Backdoor Roth Playbook: How High Earners Can Funnel an Extra $47,500 Into Tax-Free Retirement Accounts in 2026
The mega backdoor Roth routes up to $47,500 of after-tax 401(k) contributions into a Roth bucket for 2026, on top of the standard $24,500 employee deferral, by converting after-tax dollars through an in-plan Roth conversion or in-service distribution to a Roth IRA. The IRS Section 415(c) total cap of $72,000 ($80,000 if age 50+) covers contributions from all sources combined, and converting promptly keeps the taxable earnings drag near zero.
The NIL Tax Trap: What College Athletes (and Their Parents) Owe on Endorsement, Collective, and Revenue-Sharing Income
How NIL endorsements, collective payouts, and House v. NCAA revenue sharing are taxed in 2026—Schedule C mechanics, the 15.3% self-employment tax, multi-state jock-tax filings, and the planning moves that keep April manageable for college athletes and their families.
Personal Goodwill in C-Corp Asset Sales: Martin Ice Cream, Norwalk, Bross Trucking, and Howard
Personal goodwill carve-outs let C-corporation shareholders pay 23.8% capital gains instead of 40%+ combined tax on a portion of an asset sale. Martin Ice Cream, Norwalk, and Bross Trucking show when the allocation survives; Howard shows when an employment-and-noncompete agreement quietly destroys it.
Personal Goodwill in M&A Asset Sales: How Martin Ice Cream and Norwalk Help Owners Avoid Double Taxation
Personal goodwill, anchored in the Martin Ice Cream and Norwalk Tax Court decisions, lets closely held C corporation owners shift a portion of an asset-sale price out of the corporate tax layer and onto the shareholder as long-term capital gain. This guide explains the doctrine, when it works, the documentation that survives an IRS audit, and the mistakes that have sunk allocations.
Personal Holding Company Tax Under Section 541: The 20% Surtax That Quietly Ambushes Closely-Held C Corporations
Section 541 layers a 20% federal surtax on closely-held C corporations that fail both the stock ownership and 60% passive income tests. This guide walks through Schedule PH mechanics, the dividends-paid deduction, and four ways — cash, throwback, consent, and deficiency dividends — to zero out the tax before it hits.
Sales Tax on SaaS, Streaming, and Digital Goods in 2026: A State-by-State Compliance Survival Guide for Software Vendors
By 2026, sales tax on SaaS and digital goods splits into three legal routes—tangible property, taxable service, or nontaxable intangible—plus a true-object test that turns on customer intent. This guide covers the 2026 Illinois, Maine, and D.C. changes, economic nexus thresholds, and when a voluntary disclosure agreement beats direct registration.
Schedule F Survival Guide: Crop Insurance Deferral, Section 1033(e) Livestock Sales, and Schedule J Income Averaging
Schedule F farm tax elections explained — crop insurance deferral under Section 451(f), weather-forced livestock replacement under Section 1033(e), Section 175 conservation deductions, the Section 464 prepaid-supply cap, the March 1 estimated-tax rule, and Schedule J three-year income averaging — with rules, deadlines, and worked examples.
Schedule F: Farm Tax Reporting, Disaster Deferrals, and Income Averaging Explained
A practical walkthrough of Schedule F for farmers and ranchers, covering crop insurance deferral under Section 451, weather-related livestock relief (Section 451(g) and 1033(e)), Section 175 soil and water conservation deductions capped at 25% of farm gross income, Section 179 and bonus depreciation, and Schedule J income averaging using elected farm income across three base years.
Schedules K-2 and K-3 in 2026: The Domestic Filing Exception, the 1-Month Deadline, and the Foreign Tax Credit Trap
Schedules K-2 and K-3 pulled even purely domestic partnerships and S-corps into international tax reporting starting in 2021. This guide explains the 2026 filing rules, the four-condition domestic filing exception, the January 15 partner notification and February 15 1-month K-3 request deadlines for calendar-year filers, the $250,000 small entity carve-out added in 2024, and the per-partner, per-month penalty math for non-compliance.
The $2 Million Mistake: Why Gifting Appreciated Stock to Your Kids Can Be Worse Than Doing Nothing
A practical guide to Section 1015 carryover basis versus Section 1014 stepped-up basis, the dual basis trap for depreciated assets, and the 2026 decision framework for whether to gift appreciated property now or hold until death under the permanent $15 million exemption.
Section 1256 Contracts and the 60/40 Tax Rule: A Trader's Guide to Form 6781
Section 1256 splits gains on futures, broad-based index options, and qualifying forex 60% long-term and 40% short-term, capping the top federal rate near 26.8% versus 37% on equity options. A 2026 guide to Form 6781, the mark-to-market rule, and the three-year loss carryback.