The Massachusetts Legislature has set the dates for the 2026 sales tax-free weekend, and it's coming fast. The weekend of Saturday, August 8, and Sunday, August 9 will serve as this year's sales tax holiday. For years, lawmakers have set aside a weekend during the otherwise slow retail summer season to encourage shoppers to get a jump on their back-to-school shopping while pocketing the usual 6.25 percent Massachusetts sales tax. Considering you can get a better discount on almost any other weekend of the year, especially in the summer, when most shoppers would rather be at the beach, the gimmick has worked, drawing huge crowds to retail outlets across the Bay State. [more]

About one-fourth of callers to two IRS telephone lines during three months in 2025 did not receive quality customer service, a watchdog report dated June 10 said. “Recurring quality issues could lead to chronic service deficiencies and diminished taxpayer satisfaction,” the report from the Treasury Inspector General for Taxpayer Administration (TIGTA) said. The IRS agreed with the three recommendations TIGTA made in its report. TIGTA said it listened to 200 recordings of calls to Compliance Services and Accounts Management telephone lines from Feb. 15, 2025, to May 15, 2025. Of those, 52 callers, or 26%, did not receive quality customer service, the report said. [more]

Every startup begins with a handful of questions, and one of the most consequential is deceptively simple: What entity should we choose? That decision shapes how capital is raised, how founder and investor economics play out, how to design employee equity, and what the tax bill looks like upon exit. For years, venture–backed companies defaulted to C corporations to unlock qualified small business stock (QSBS) gain exclusion under Sec. 1202, while bootstrapped or profitable businesses favored passthroughs to take advantage of the Sec. 199A qualified business income (QBI) deduction and manage self–employment tax, all while maintaining flexibility with exit strategies. [more]

It's a tale as old as time: If you live in a high-cost area like Long Island, San Francisco, or Seattle, your paycheck doesn't stretch nearly as far as it would in, say, Pittsburgh. Yet, the IRS taxes your income exactly the same. A new bill from lawmakers on Capitol Hill would flip that script by linking your federal tax obligations to your home address. The Cost of Living Tax Cut Act, introduced by House Reps. Laura Gillen (D-NY-04) and Mike Lawler (R-NY-17) would adjust federal income tax brackets based entirely on where a taxpayer lives. "This bipartisan bill would help lower taxes for families in high-cost areas [like Long Island] by accounting for regional differences in the cost of living and ensuring taxpayers can keep more of what they earn," Gillen said in a recent release. [more]