Navigating Challenges as a First-Time Short-Term Rental Host

This chapter explores the hurdles first-time hosts and property managers encounter in the short-term rental space. It underscores the importance of property understanding, insurance, maintenance costs, and the impact of cleanliness and quality furnishings on guest satisfaction.

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#559 If you’ve ever dreamed of owning an Airbnb or glamping getaway, this episode is your crash course in how to make it happen! Host Brien Gearin is joined by Garrett Brown, short-term rental investor and glamping expert at BiggerPockets, to break down the business of hosting — from buying your first property to optimizing your listing and maximizing profitability. Garrett shares his personal journey, practical advice for first-timers, and insider strategies for managing operations, choosing the right market, avoiding costly mistakes, and leveraging tools to automate and scale. Whether you’re starting with a small condo or aiming for a luxury lakefront cabin, this episode is packed with actionable insights to launch and grow your short-term rental business!

What we discuss with Garrett:

+ Garrett’s journey into short-term rentals

+ Why he pivoted from traditional real estate

+ The reality of managing Airbnbs

+ The 60/30/10 market selection rule

+ Glamping and unique stays explained

+ Best property sizes for STR success

+ Must-use tools like PriceLabs and HostBuddy

+ Airbnb vs. VRBO pros and cons

+ Listing optimization tips for more bookings

+ When (and why) to self-manage your rental

Thank you, Garrett!