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#tax-compliance

Tax Compliance

Stay compliant with tax regulations and filing requirements

PayPal and Venmo Are Finally Talking: What the End of Visa+ Means for Freelancers Before February 2026

Starting February 19, 2026, Visa+ stops working for PayPal and Venmo transfers and is replaced by direct phone-number payments rolling out November 2025. With the 1099-K threshold falling to $600 in 2026, freelancers must tag inter-app transfers correctly, reconcile gross versus net per platform, and separate business from personal flows to avoid double-counting income.

Short-Term Rental Co-Host Bookkeeping: How to Reconcile Double-Reported 1099-Ks Without Overstating Income

Airbnb reports the full gross booking on the owner's 1099-K and your co-host share again on yours — so $80,000 in real bookings can appear as $96,000 to the IRS. This guide explains the 2026 OBBBA changes ($20,000 and 200 transactions for 1099-K, $2,000 for 1099-NEC), which form you should receive, and the chart-of-accounts method to reconcile gross vs. net without overreporting income.

The $2,000 1099-NEC Threshold for 2026: W-9s, Backup Withholding, and the Vendor Playbook That Keeps You Penalty-Free

For payments made on or after January 1, 2026, the federal 1099-NEC/1099-MISC reporting threshold rose from $600 to $2,000 under P.L. 119-21 — but royalties ($10), attorney gross proceeds ($600), and backup withholding on any withheld amount are unchanged. Here is the vendor-onboarding and W-9 workflow that prevents penalties either way.

Canada Canceled Its Digital Services Tax: How to Claim Your Share of the $647 Million Refund and Fix Your Books

Canada repealed its 3% Digital Services Tax and the CRA is returning about CAD $647 million — $289 million in cash and $358 million offset against other tax debts. Direct filers get automatic refunds with interest; Amazon and Etsy sellers who paid the DST pass-through surcharge get no CRA claim and must reconcile and reclassify those fees themselves.

The DOL Wants to Scrap Its Six-Factor Contractor Test: What the 2026 Two-Factor Proposal Means for Your Business

The DOL's February 26, 2026 proposal (RIN 1235-AA46) would replace the 2024 six-factor contractor test with a two-factor economic-reality analysis weighing control and opportunity for profit or loss. Here is what changes, why the 2024 rule is in enforcement limbo, and what to document in your books now while the rescission is pending.

Illinois' Swipe Fee Ban on Sales Tax and Tips: What the Interchange Fee Prohibition Act Means for Your Business Before July 2026

Illinois' Interchange Fee Prohibition Act bans swipe fees on the sales tax and gratuity portions of card transactions starting July 1, 2026 — the first US law of its kind. Learn how to prove tax and tips per transaction, choose between the real-time exemption and the 180-day rebate, and structure a chart of accounts that captures every dollar either way.

Pay As You Go: How Small Businesses Avoid the Estimated Tax Underpayment Penalty With Safe Harbor Rules for 2026

Hit one estimated-tax safe harbor and the IRS underpayment penalty disappears — pay 90% of this year's tax or 100% of last year's (110% if prior-year AGI topped $150,000) through timely quarterly payments. Covers the 2026 penalty rate (7% Q1/Q3, 6% Q2, compounded daily), the four due dates, and a bookkeeping system that keeps you penalty-free.