49:26

In this open‑forum episode of the Main Street Business Podcast, host Matt Sorenson and tax‑law expert Mark J. Kohler answer a rapid fire series of listener questions covering the most common tax and legal dilemmas faced by side‑hustlers, small‑business owners, and real‑estate investors. The conversation moves from a high‑level recommendation that any business netting $40K+ should elect S‑corp status, through nuanced discussions of self‑rental rules, cost‑segregation, real‑estate‑professional status, and the tax implications of moving personal residences into LLCs. They also cover practical issues such as foreign‑entity registration for nomadic entrepreneurs, paying children for legitimate work, prohibited‑transaction rules for IRA‑LLCs, step‑family transactions, holding‑company structures inside a Solo 401(k), Medicaid and estate‑planning look‑back periods, and the proper allocation of purchase price in business acquisitions. Throughout, the hosts blend informal, conversational tone with actionable, often‑cautious advice, urging listeners to consult qualified tax or legal professionals for personalized guidance.

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