In Clay of Life, Menachem and Yossele are homefree, being itinerant blacksmiths. They have helped other people who are homefree, homeless, or working poor. This is considered a normal and successful lifestyle in their culture.
A Conflagration of Dragons is about what happens when multiple strikes take out all the major cities, making everyone homeless. It is neither normal nor healthy, but it's what everyone gets stuck with after the dragons burn down all the cities and eat the heroes.
Diminished Expectations has a lot of homeless characters, but that series is outright dystopic. It is ubiquitous, but not very good for anyone.
Frankenstein's Family has the Caldarari caravan and assorted other traveling people who are homefree. Opinions vary about how respectable this is.
The Origami Mage, Path of the Paladins, and Sort of Heroes are probably best described as having homefree protagonists who travel. Reception varies, but seems more positive than negative.
Polychrome Heroics has a bunch. Cassandra ran away from home for valid reasons, and is currently living with a friend; not homeless in the sense of having nowhere to go, but also not having a home of her own. Danso and Family started out homeless but have since found a home. Officer Pink features Turq, who starts out homeless and is trying to get to where he'd feel comfortable having a home again; Nebuly, who's switching from homeless to homefree; and assorted other characters along that spectrum. Terramagne-America is more supportive of homefree and more accepting of homeless people than local-America is.
So you can see a pretty wide range of portrayals above. If this topic interests you, feel free to prompt for more of these characters, or suggest others. I am especially interested in getting such input from readers who are or have been homeless or homefree.