As a kid growing up in Ouray, living in his parents’ trailer on Oak Street, David Huddleston never imagined that at 36, he’d still be living there.

Buying a house in his hometown seemed out of reach, but he figured he’d be able to rent a place on his own.

Instead, he’s sleeping in a 9-by-9 room, searching unsuccessfully for a place to live with his 27-year-old sister and their three dogs.

“I’m back where I was when I was 5 years old,” he said, sitting on the mattress that takes up mos...