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Is your short-term rental strategy stuck in 2025? In this episode of The Check-In, hosts Sarah and Leo sit down with one of the STR industry's brightest stars, Hailie Maarie, who has built a staggering 70-property empire in just four years. Hailie breaks down her "2026 Host Checklist"—the essential moves that separate surviving hosts from those who scale.
We dive into why "throwing a listing on an OTA" is no longer enough, how to build a brand that attracts both owners and guests, and the secret to balancing high-tech AI with a high-touch human experience. Whether you’re just starting or looking to "cut the fat" from your portfolio, Hailie shares the mindset shifts and systems required to stay relevant in an increasingly competitive market.
By Leo Walton and Sarah Nan DupreIs your short-term rental strategy stuck in 2025? In this episode of The Check-In, hosts Sarah and Leo sit down with one of the STR industry's brightest stars, Hailie Maarie, who has built a staggering 70-property empire in just four years. Hailie breaks down her "2026 Host Checklist"—the essential moves that separate surviving hosts from those who scale.
We dive into why "throwing a listing on an OTA" is no longer enough, how to build a brand that attracts both owners and guests, and the secret to balancing high-tech AI with a high-touch human experience. Whether you’re just starting or looking to "cut the fat" from your portfolio, Hailie shares the mindset shifts and systems required to stay relevant in an increasingly competitive market.