Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler tackle one of the most pressing issues in real estate and hospitality—the growing wave of short-term rental regulations. From Boston and Portland to vacation markets like Cape Cod and Bar Harbor, they break down how local governments are shaping the landscape and what it means for investors, operators, and homeowners.

Dave and Will explore whether regulations are killing innovation or simply protecting neighborhoods. They highlight the differences between metropolitan markets, where affordability and neighborhood impact are driving restrictions, and vacation markets, where safety and infrastructure are the focus. The conversation also dives into the opportunities these changes create—such as boutique hotels, ADUs, and other creative strategies that thrive within regulatory frameworks.

Whether you’re considering your first investment property or already operating multiple units, this episode delivers essential insights on zoning, HOA rules, due diligence, and the importance of common sense in real estate investing. Tune in now to learn how to navigate regulation with confidence, spot hidden opportunities, and avoid costly mistakes.

TIMESTAMPS

01:57 – Why regulation isn’t always a bad thing

02:58 – Metro and vacation markets

03:53 – How regulations shape neighborhoods

05:41 – Boutique hotels create opportunities where STRs are restricted

07:14 – Creative approaches with ADUs and owner-occupied rentals

08:47 – HOAs: hidden rules that can make or break your investment

10:37 – Due diligence and using common sense before buying

11:40 – Why relationships and neighbor dynamics matter for operators

12:43 – Deal analysis, and avoiding bad buys

13:53 – Why AI tools fall short on regulation research

14:43 – How to connect with Dave and Will

#ShortTermRentals #RealEstateInvesting #STRRegulations #BoutiqueHotels #PropertyManagement