Episode 139: Avoid IRS Penalties!

In this episode: Why most taxpayers don't itemize anymore, and when it still actually makes sense to do so The hidden fine print on mortgage interest deductions, including caps that quietly limit what high-balance homeowners can write off How home equity loans can either save you on taxes, or cost you the deduction entirely depending on how you use the money The real story behind points, refinancing, and why timing matters more than most people realize Why some common "write-offs" like mortgage insurance premiums rarely benefit higher earners A major shift in state and local tax deductions, and why some business owners may suddenly see bigger write-offs The growing cost pressure of employee health insurance, and the moment your business is legally required to offer it How benefits strategy isn't just an expense, it's a recruiting weapon if you play it right A surprising tax change around gambling income that quietly increases what people owe Why the IRS insists you pay taxes throughout the year, not just in April, and how that impacts cash flow The concept of "safe harbor" payments and how it can protect you even if your income swings wildly A lesser-known payroll strategy some business owners use to legally manage timing of tax payments Why tax planning isn't just a nice-to-have, it's the difference between scrambling in April and being in control year-round