#tax-planning
Strategic tax planning to minimize liability and maximize savings
Illinois eliminated its 200-transaction economic nexus threshold under HB 2755 effective January 1, 2026, leaving a single $100,000 revenue test and offering a limited amnesty window from August 1 to October 31, 2026 for unregistered remote sellers.
Powerboat and pontoon rental income is reported on Schedule C, not Schedule E, which subjects net profit to the full 15.3% self-employment tax — a distinction that shapes how these seasonal businesses should handle depreciation, off-season cash reserves, and an eventual S-corp election.
A 1% federal excise tax applies to cash-funded international money transfers starting January 1, 2026, but bank, debit, and credit card transfers are exempt — here's how small businesses can avoid it.
Section 125 cafeteria plans must pass three IRS nondiscrimination tests each year — eligibility, benefits and contributions, and the 25% key employee concentration test. This guide covers the 2026 thresholds ($220,000 officer and $160,000 HCI compensation, $3,400 FSA and $7,500 DCAP limits), what a failed test costs your top earners, and when a Simple Cafeteria Plan under Section 125(j) lets employers with 100 or fewer employees skip testing entirely.
Cost segregation studies routinely move 16–24% of a self-storage facility's purchase price off the 39-year schedule into 5- and 15-year property. With 100% bonus depreciation permanently restored by the OBBBA for property placed in service after January 19, 2025, a $1 million acquisition can produce roughly $200,000 in first-year deductions — about $74,000 in tax savings at a 37% rate. Here's how the studies work, what they cost, and the recapture math to run before selling.
The 2026 Social Security wage base rises to $184,500 from $176,100, pushing the maximum employer-side Social Security tax per employee up $520.80 to $11,439, and resets to zero separately for every employer a highly paid employee joins mid-year.
A freelancer earning $80,000 net self-employment income can shelter roughly $43,070 in a Solo 401(k) versus $18,570 in a SEP IRA in 2026 — the gap comes entirely from the $24,500 employee-deferral bucket that SEP IRAs don't offer.
Under SECURE 2.0, workers who turn 60-63 in 2026 can defer up to $35,750 into a 401(k) — but anyone whose prior-year FICA wages topped $150,000 must make the entire catch-up as Roth, and loses it entirely if their plan lacks a Roth option.
How an ESOP lets founders exit on their own terms — 6,411 US ESOPs hold $2.1 trillion for 15.1 million employees. Covers Section 1042 capital gains deferral, the S-corp federal tax exemption, 2–4% deal costs, fiduciary and repurchase obligations, and which businesses actually fit the structure.
Late Schedule K-1s are the norm, not the exception — a Form 7004 extension pushes partnership and S-corp returns, and every K-1 tied to them, to September 15, a full five months past the April 15 personal deadline. The fix is a simple playbook, file Form 4868, pay at least 90% of a good-faith estimate, and amend with Form 1040-X once the real numbers arrive.
A cash balance plan is an IRS-qualified defined benefit plan that lets business owners 45 and older stack $75,000 to $290,000 in additional pre-tax retirement contributions on top of a 401(k), with the trade-off being a required multi-year funding commitment and $2,000-$4,000 in annual actuarial administration costs.
An Employee Ownership Trust (EOT) lets a business owner sell to a permanent employee-benefit trust instead of a competitor or private equity firm, costing roughly $30,000-$100,000 to set up versus $150,000+ for an ESOP, though the U.S. still offers no federal tax incentive for EOT sales while Canada made its C$10 million capital gains exemption permanent in June 2026.
