Short-Term Rental Regulation in Michigan: What Investors Get Wrong | STR Panel

Short-Term Rental Investing in Today's Market

Short-term rental investing has changed faster than almost any other real estate strategy, and the rules that made deals work in 2021 are actively losing money in 2026. This panel was recorded live at the 2026 Midwest Real Estate Investor Conference, where moderator Jeremy Garcia sat down with three operators who have been through the regulatory grinder: commercial investor and broker Charlie Kao, Michigan short-term rental attorney Katie Johnson, and designer and vacation rental investor Sarah Doane. They cover market selection, Michigan zoning and deed restrictions, what actually separates a profitable Airbnb from one that is just getting by, and where the real opportunities sit now that the easy money is gone.

About the Panel

Charlie Kao is an investor, broker, and principal at Twin Oaks Capital with more than twenty years in short-term rentals and hospitality real estate. An early Airbnb adopter, he now operates across five states including Florida, Tennessee, North Carolina, and Virginia, and provides consulting, brokerage, and feasibility studies to owners and investors.

Katie Johnson is a Michigan real estate attorney and founder of Katie Johnson PLC and STR Law. She advises short-term rental owners nationwide on asset protection, zoning, and compliance, and helps long-term landlords with lease drafting and risk management. She is also an active investor who owns and manages roughly eleven properties in Southwest Michigan.

Sarah Glidewell is an interior designer and vacation rental investor with more than a decade of design experience. Since 2019 she has focused on designing short-term rentals built around guest experience, and she invests in rural lake and river markets in Michigan and Upstate New York alongside her husband.

Jeremy Garcia moderated the panel. He operates short-term rentals and a boutique hotel in the Muskegon market.

What We Cover in This Episode

How to evaluate a short-term rental market when regulation is unsettled Why highly regulated markets can be safer than unregulated ones Michigan short-term rental case law and why owners are not automatically grandfathered Deed restrictions, title work, and the covenant language that shuts operators down The Park Township ban, the ongoing federal lawsuit, and what it means for other municipalities What happened when three of four short-term rentals were shut down by regulation Using 1031 exchanges to move out of markets that turn hostil