This week’s roundup covers Airbnb’s 2026 Summer Release, AI’s growing role in the guest booking journey, Booking Holdings’ long-term growth strategy, Nashville preparing for the 2030 Super Bowl, and a proposed statewide short-term rental tax in Illinois. Let’s dive in.

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This week, we are featuring Tom May, founder of Fade Away Vacations. Tom has been partnering his business with OwnerRez since 2022, and what started as a small personal investment has grown into a portfolio of thoughtfully designed homes focused on helping guests “fade away” and create meaningful stays.

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In Episode Thirteen, Paul and Chris break down the undervalued power of saying no and how that clears the way for the right yes. They talk through recent investment decisions, how their thinking has shifted over time, and how to recognize a property with the right “feeling.”

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This week’s roundup covers World Cup-driven demand, housing concerns in major event markets, short-term rental enforcement in Hawaii, and new data on professional property managers.

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Meet Tanya Lee, owner of Vivaro Roatan, a collection of luxury villas in the Caribbean. Inspired by her love for travel and a desire for consistent quality, she’s built a strong hospitality brand focused on delivering five-star service and thoughtful amenities.

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