#tax-compliance
Tax Compliance
Stay compliant with tax regulations and filing requirements
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.
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.
Temporary Sales Tax Permits for Pop-Up Shops and Holiday Markets: What Vendors Need Before the First Sale
Nearly every state requires sales tax registration before your first pop-up or holiday market sale, but the mechanism varies — California issues a free temporary seller's permit, New York demands a full Certificate of Authority, and Utah licenses each event separately. A state-by-state breakdown, the five mistakes that cost vendors money, and a pre-event compliance checklist.
No Mileage Log, No Deduction: What Simmons v. Commissioner Teaches About Vehicle Expense Substantiation
In Simmons v. Commissioner (T.C. Memo. 2026-34), the Tax Court disallowed a $12,939 vehicle deduction because QuickBooks entries and lease agreements failed the four-element substantiation test of IRC Section 274(d) — amount, time, place, and business purpose. Here's what a mileage log must contain, why the Cohan estimation rule can't save you, and how the same entity-level documentation gap cost the taxpayer interest and utility deductions plus a 20% negligence penalty.
The Tax Court Just Redefined "Funded Research" for the R&D Credit — and Most Client-Funded Firms Are About to Fail It
In Smith v. Commissioner (T.C. Memo. 2026-50), the Tax Court denied an architecture firm's R&D credit on two of six client projects because IP-assignment and reuse-approval clauses forfeited "substantial rights," and limited four more to research expenses exceeding client payments — putting standard architecture, engineering, and consulting contracts on notice.
Sneaker Resale Bookkeeping: Cost Basis, Cop-and-Flip Inventory Tracking, and Why StockX/GOAT 1099-Ks Rarely Match Your Actual Profit
A 1099-K from StockX or GOAT reports gross payments, not profit. Here's how sneaker resellers track per-pair cost basis, apply FIFO to cop-and-flip inventory, deduct platform fees that run 10-12% per sale, and meet the restored $20,000/200-transaction reporting threshold with clean books.
Thermal Circuits v. Commissioner: Why Customer-Funded Facility Expansions Are Taxable Income
In Thermal Circuits, Inc. v. Commissioner, the Tax Court held that $4.3 million a customer paid to expand a manufacturer's facility was taxable income, not an excludable Section 118 capital contribution — because Thermal controlled the asset, the money was compensation for guaranteed capacity, and post-TCJA Section 118(b) excludes any customer contribution or contribution in aid of construction. What the ruling means for prepayments, tenant improvement allowances, and capacity deals.
One Missing Sentence Cost a Donor a $4.4 Million Charitable Deduction — What Wells v. Commissioner Requires of Your Acknowledgment Letter
In Wells v. Commissioner (2026), the Tax Court disallowed a $4.42 million charitable deduction for donated real estate because the charity's acknowledgment letter was undated and never stated whether the donors received goods or services in return — Section 170(f)(8) demands strict, not substantial, compliance. The 20% accuracy penalty was abated only because the donors documented good-faith reliance on their CPA.
White v. Commissioner: Can the IRS Levy You While You're Current on a Payment Plan?
In White v. Commissioner (T.C. Memo. 2026-56), the Tax Court blocked an IRS levy on a taxpayer who was current on a court-approved installment settlement, holding the levy violated Section 6330's "no more intrusive than necessary" standard. What the ruling means for anyone on an IRS payment plan, and why a CDP hearing request within 30 days is the critical first move.
Bitcoin Mining Bookkeeping: Why Every Mining Pool Payout Is Its Own Taxable Event
Under IRS Notice 2014-21, every mining pool payout is ordinary income at its fair market value on receipt — a daily-payout pool creates ~365 taxable events a year before you sell anything. This guide covers hobby vs. Schedule C classification, 15.3% self-employment tax, Section 179 vs. 100% bonus depreciation for ASICs, the 2026 per-wallet cost-basis rule, Form 1099-DA reconciliation, and the per-lot records mining books need to survive an audit.
Canada Killed the Underused Housing Tax. If You Own Property There, Your Paperwork Isn't Done Yet.
Canada repealed the federal Underused Housing Tax for 2025 onward on March 26, 2026, but the repeal is not retroactive — US owners of Canadian property still owe UHT returns, penalties, and interest for 2022–2024, and BC's Speculation and Vacancy Tax, Vancouver's Empty Homes Tax, and Toronto's Vacant Home Tax remain in force.
Esports Organization Bookkeeping: Prize Pools, Sponsorships, and the New 1099 Threshold
Esports organizations must separate prize revenue from player distributions, recognize sponsorship revenue under ASC 606 as obligations are delivered, and track the 2026 rise of the Form 1099-NEC/MISC filing threshold from $600 to $2,000 per payee.