As a road manager on a bunch of big name music tours, Angela spends eight months a year living on a sleeper bus. Every day she rolls into a new city, sets up a production office, manages the event, and packs up again. When a tour wraps up, she usually heads back to her hometown of Kansas City, and crashes with her mom.

Drew Smith is a Navy doctor who's been deployed to San Diego. He and his wife, Libby along with their two dogs, have moved into a temporary apartment downtown until they can find a 700 square foot craftsman home in the historic streetcar neighborhood of North Park. Original built-ins and vintage charm abounds in the area's prewar homes, something Libby loves.

Jenn and her boyfriend, Jason, are hunting for a tiny retreat on the Big Island of Hawaii, in Kona. Jenn is a busy single mom and a passionate artist. Jason is an elite US smoke jumper, who often lives out of his 100 sq ft van for months at a time, while on location putting out wildfires. With their hectic schedules they know the perfect tiny getaway in Kona, a place they both love, will give them a place to relax and reconnect.