Tomorrow night, wandering indie-folk troubadour David Dondero swings back into town to play a show at the Comet. Dondero — touring behind his recently released (and quite excellent) seventh solo album, Simple Love — is a masterful storyteller, weaving humor and tragedy together in ways few others can as he spins tales from America’s backroads, about unique and conflicted characters (sometimes it’s fiction, sometimes it’s barely disguised autobiography). The 38-year-old singer has been dedicated to the road for the past decade-plus, so much so that he’s essentially homeless — driving around the country to play shows, renting rooms or crashing on friends’ sofas, working occasional odd jobs in various cities, and reducing his worldly possessions to his guitar, an amplifier, and one bag’s worth of clothes and necessities. “When I’m stuck in some place for a while I gotta get outta there,” Dondero explained to me not long ago. “It ruins certain things and confuses certain things, and in other ways it brings clarity, thrusting yourself out there and taking a gamble. I think it’s fine to be aimless and not have it figured out. I’ve always thought that as soon as you have it figured out, you’re dead, you know?” Still, he admitted, he’s conflicted about his nomadic ways — a struggle that plays out in many of his affecting songs. “Maybe I don’t wanna be alone all the time. It’s like a battle of being in love with the lifestyle of traveling around, and being in love with the idea of being in love, and realizing that it’s not possible to have both. I’d like to have a relationship, to settle down and have a family someday. I can see it and it looks like a nice vision, but it’s probably not realistic.”