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 hostile
• Whether the short-term rental market is actually oversaturated
• How to read AirDNA data without drawing the wrong conclusion
• Rising costs, shrinking margins, and the shift in Airbnb guest fees
• Bringing cleaning in-house and what it does to cleaning cost per turn
• Using AI for guest messaging and after-hours support
• Guest avatar selection and how it drives every design decision
• Which amenities actually produce return, including hot tub revenue data
• Hedging seasonality with year-round amenities in cold weather markets
• Short-term rental tax strategy, depreciation, and offsetting outside income
• The luxury design gap that most operators are ignoring
• Working with municipalities: grassroots campaigns, local counsel, and goodwill with neighbors
• The biggest mistakes each panelist made and what they cost

Key Insight

Sarah Glidewell and her husband had four fully operational short-term rentals in Michigan when the state pushed regulation down to the local level. Over two years, three of the four were shut down. They 1031 exchanged all of them into new properties, and every one sold for over asking price within the first week on the market. They did not lose money. They lost time, and they lost the compounding. Her takeaway: she now buys nothing without legal review first, and she deliberately targets markets that are already regulated.

Why This Episode Matters

If you are underwriting a short-term rental in an unregulated market because it looks like open runway, this panel gives you the case law and the operator experience explaining why that assumption can cost you the asset. It also gives you a concrete answer on saturation, on which amenities produce measurable revenue lift, and on what a professionalized short-term rental operation actually looks like now that mom-and-pop listings no longer compete.

Find Out More

Charlie Kao
Website: twinoakscap.com
LinkedIn: linkedin.com/in/charliekao
Instagram: @charlesckao
YouTube: Twin Oaks Capital

Katie Johnson
Websites: strlaw.com and katiejohnsonplc.com
Podcast: STR Law
Instagram

Sarah Glidewell
Instagram

Jeremy Garcia
Website: bookdreamstay.com

Midwest Real Estate Investor Conference

This panel was recorded live at the 2026 Midwest Real Estate Investor Conference. The 2027 conference is scheduled for May 20 and 21, 2027. If you want a full two days of sessions like this one, plus direct access to the operators, investors and attorneys actually doing this work in the Midwest, put it on your calendar now. Details and registration at midwestreiconference.com.

Sponsors

Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area.
https://www.livegreenlocal.com

And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits.
https://www.rcbassociatesllc.com