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Tax
Tax strategies, planning, and compliance for individuals and businesses
Cannabis Schedule III Rescheduling: What 280E Tax Relief Actually Means for Your Dispensary
On April 22, 2026 the DOJ moved certain state-licensed medical marijuana products from Schedule I to Schedule III, ending Section 280E's ban on ordinary business deductions for qualifying operators — while recreational-only dispensaries remain fully subject to 280E's COGS-only tax treatment.
Clinco v. Commissioner: A Tax Court Judge Flags AI-Hallucinated Case Law — What It Means for Business Owners Using AI
In Clinco v. Commissioner (T.C. Memo. 2026-16), Judge Mark Holmes flagged three nonexistent case citations that "suggest something cooked up by AI" — the first such warning from the U.S. Tax Court. With 1,598 documented AI-hallucination court cases by June 2026 and sanctions topping $145,000 in Q1 2026 alone, here is what business owners using AI for tax and financial paperwork need to verify.
The Deferred Sales Trust: How Business Owners Defer Capital Gains on an Exit Without a 1031 Exchange
A deferred sales trust lets a business owner spread capital gains tax from a sale over 10-20 years under IRC Section 453 with no like-kind reinvestment requirement, but setup and management fees commonly total $100,000-$300,000+ over a decade and the IRS has never issued formal guidance approving the structure.
Discord Server Subscriptions and the 1099-K: Why Your Tax Form Shows More Than You Were Paid
Discord issues 1099-Ks through Stripe reporting gross subscriber payments, not your net payout after the ~10% platform fee, Stripe processing, and app-store cuts. Here's how server owners reconcile the gap on Schedule C, what the restored $20,000/200-transaction federal threshold means for 2026, and the self-employment tax that applies either way.
The New Federal Scholarship Tax Credit (ECCA): What Small Business Owners Should Know Before 2027
The Educational Choice for Children Act creates a $1,700 federal income tax credit for cash donations to K-12 Scholarship Granting Organizations, starting with the 2027 tax year — but only in states that opt in. Here is how the nonrefundable, cash-only Section 25F credit works, the five-year carryforward, the 90% pass-through rule for SGOs, and why pass-through business owners should track their state's participation through 2026.
Bookkeeping for Freelance Translators and Interpreters: Rates, Rush Fees, and Currency Spread
A freelance translator invoicing €450 can receive as little as $431 due to a 3%-4% PayPal exchange-rate markup that never appears as a labeled fee, which is why translators and interpreters need to log invoiced and received amounts as separate figures and post the difference to a dedicated Bank & FX fees expense category.
Hawaii Storm Tax Relief: What the August 20, 2026 IRS Deadline Covers — and the Earlier State Deadline It Doesn't
The IRS postponed tax deadlines to August 20, 2026 for Honolulu, Maui, and Kauai counties after the March 2026 Kona Low storms — but Hawaii's separate Form L-115 state relief closes July 20, and SBA loan deadlines fall on August 13, 2026 (physical damage) and January 7, 2027 (EIDL). Here's who qualifies, what's automatic, and the casualty-loss election that can accelerate a refund.
Hee v. Commissioner: How $2 Million in Personal Expenses Became Constructive Dividends and a 75% Fraud Penalty
In Hee v. Commissioner, the Tax Court found a sole shareholder ran over $2 million in personal costs — massages coded as consulting, MIT tuition, family vacations, and $1.1 million in undocumented loans — through his corporation, upholding a 75% civil fraud penalty under IRC Section 6663 and offering small-business owners a checklist for shareholder loans, related-party pay, and expense substantiation.
Ireland's Budget 2026: What the VAT Cut and New Reliefs Actually Mean for Small Business Owners
Ireland cut VAT on food, catering, and hairdressing from 13.5% to 9% on July 1, 2026, raised the entrepreneur relief cap to €1.5M, and boosted the R&D credit to 35% — but the minimum wage hike to €14.15 and pension auto-enrolment landed six months earlier. Here's what each change means for small business books.
Maryland and Washington Now Tax B2B Tech Services: What Sellers Owe in 2026
Maryland's 3% tech-services tax (effective July 1, 2025) and Washington's ESSB 5814 (effective October 1, 2025) made IT consulting, custom software, data processing, and digital advertising taxable — even for out-of-state sellers past economic nexus thresholds. Here's what's taxable, the contract-renewal trap, and a compliance checklist.
NAR's $52.25M Tuccori Settlement: What It Means for Real Estate Agent Bookkeeping
NAR's $52.25 million Tuccori settlement, approved April 10, 2026, doesn't change buyer-agent commission rules — it makes the August 2024 Sitzer/Burnett practice changes permanent, so agents must book gross commission across multiple funding sources rather than treating deposits as a single income line.
The OBBBA's Gambling Loss Cap Means You Can Owe Tax on Money You Never Actually Won
Starting in tax year 2026, the OBBBA caps gambling loss deductions at 90% of winnings, meaning gamblers and gaming-adjacent businesses can owe tax on breakeven or even losing years, prompting three bipartisan repeal bills in Congress.