I have a faint memory of watching a Japanese drama several years ago about a guy who had mastered the art of being homeless and could stay clean and well dressed and have a good job without having a home. And I think he was a philanthropist who spent all his money on doing good things and donations or whatever, which was also why he didn't have a home. I guess it's also possible it was a Manga i read... :/

Anyhow, any drama that has a similar plot? 

Okay, that description does sound familiar, but for the life of me, I couldn't remember what that is.

But anyway, the most "pro-homeless" drama that I've watched was Kawa no Hotori de, mostly because they portray homelessness as this neutral thing, as in yes, not having a home is challenging, but people are people.