Experts warn that self-employed individuals and landlords are unprepared for new tax regulations.

New Digital Tax Rules Set to Impact Landlords and Self-Employed Workers Advisers are sounding the alarm as hundreds of thousands of landlords and self-employed individuals face potential challenges from new digital tax payment rules set to take effect in 2026. There’s been a noticeable lack of awareness regarding what some are calling the “biggest change […]
Withdrawing from a 401K. Returning to work. Concerns about ACA expenses for the self-employed.

Updated December 11, 2025 at 10:30 a.m. ET Krisa Ostenzo anticipates having to withdraw from her savings to afford her $1,500 monthly health insurance plan once the extended tax credits from the Affordable Care Act (ACA) run out next year. She and her husband managed an optometry practice in rural Wisconsin for 35 years until […]