The Short Term Shop team shares a wide-ranging 2027 outlook for short-term rental investors. They discuss the buyer’s market in vacation destinations, interest rates and financing strategies, rental performance expectations, changing booking platform fees and policies, and the growing role of AI in guest operations and property research. CPA guests Matt and Amanda explain depreciation and the short-term rental tax strategy, including material participation and carrying unused losses forward. Agent Natalie offers guidance on using AI during the buying process: use it to research and organize information, while building understanding through conversations with local professionals. The team also reviews software developments in guest messaging, cleaning coordination, pricing, and property amenities, and closes with advice on keeping accurate, real-time records of time spent working on a rental.

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For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon