Some college kids in one of my classes toured across the U.S. on Surly and All-City bikes this past summer. Some had Ortliebs, some had handmade bags, all had grundgy clothes and duct-taped windbreakers and other artifacts of actually using their equipment.
They looked like homeless 20-year-olds. And they had a blast. And they returned to shower and study and start careers.
I don't look homeless when I tour; I look like myself. I just do what I want. So did these kids from UMass. So do most tourists. It's harder to judge people from a bike saddle than from a yacht or luxury car, and that's what I like about them so much. Please don't spoil that with some projected sense of "real" touring vs. "homelessness."