What happens when two hands-on STR operators decide to take their kids, their business, and a camera across all 50 states? Kylee and Steven Niederhauser—longtime hosts and boutique property managers in Southern California and the Palm Springs region—join Jamie to share the remarkable evolution of their business and the surprising realities of running 40+ units from the road.

In this episode, they unpack how they went from a rundown Mission Beach duplex to a curated, mid-size management portfolio—without ever aiming to become “big.” Their story is a masterclass in staying lean, staying connected, and building systems that support real freedom… not just more work. Along the way, they’re gathering fresh inspiration from dozens of stays across the country, rethinking what truly makes a memorable STR experience, and learning what hosts get right (and wrong) from a guest’s perspective.

Whether you’re an aspiring host, an already-stretched operator, or someone dreaming of reshaping your lifestyle through STRs, this episode distills years of hard-earned lessons—no fluff, just practical insights from operators living it in real time.

You don’t want to miss this episode.

🔑 Key Takeaways

Boutique beats big: Kylee & Steven intentionally chose not to scale endlessly—quality, owner alignment, and lifestyle mattered more than unit count.
Systems enable freedom: Their remote-friendly stack centers around Uplisting + Breezeway, with smart-home tools filling the gaps.
Personalized responses still win: They use templates—but not automation—so every guest feels a human touch (and messages never sit unanswered).
Owners must buy in: Performance issues often come down to owners unwilling to reinvest; showing real comps is key to shifting mindsets.
Being guests changed their hosting: Their 50-state trip revealed what truly matters to travelers—and inspired new ideas for design, amenities, and guest experience.