51:21

In this open‑forum episode of the Main Street Business podcast, tax attorney Mark J. Kohler and CPA Matt Sorensen answer a rapid‑fire series of listener questions covering a wide range of tax, estate‑planning and business‑entity issues. They begin with a real‑world story about a grandmother whose house was liened because her son was on the deed, illustrating the danger of improper title planning. The hosts then discuss elder‑law Medicaid clawbacks, the limited usefulness of Lady Bird deeds versus revocable living trusts, and the tax‑treatment of health‑savings accounts (HSAs) and self‑directed IRAs. They compare LLCs, S‑corporations and sole‑proprietorships for rental, consulting and bookkeeping businesses, emphasizing when an S‑corp election saves payroll taxes and how to convert an LLC. They debunk the myth that a large liability insurance policy replaces the asset‑protection of an LLC, and they explain mileage deduction rules, child‑worker reporting (1099 vs. W‑2), and the tax consequences of winning a charitable‑raffle house. The episode also covers crypto‑IRA airdrops, the impact of a “step‑up in basis” on Lady Bird deeds, and the importance of proper estate‑planning documents (trusts, powers of attorney, health directives). Throughout, the tone is conversational and instructional, with a supportive yet cautionary sentiment toward listeners who rely on inadequate advice. The hosts repeatedly urge listeners to seek qualified tax‑legal counsel and to avoid “poor accountants.”

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