My definition of a hobo is a person of no fixed abode who moves around a lot - quite different from a homeless person. It would be a big red flag to me. I’d wonder why they didn’t have any kind of permanency in their life. People like that usually have serious issues, and I’m not naive enough to think I could ‘sort’ them. Having a core of responsibility is important to me, so I wouldn’t find them attractive - no matter how pretty they were on the outside.