I've been lurking a while just reading about the chumby and just decided to join. It sounds like it's going to be awesome when it's released. I don't really know much about the chumby, flash, or programming in general, apart form a little VB.
projectplaylist.com is a website that allows you to make playlists for your myspace, facebook, blog or any other page you might have.
I believe that the playlists are flash programs. Could a parternership of sort be devised so you stream the playlists to a widget on your chumby? From browsing around on the forum, i saw that there are some issues with streaming MP3's, and that chumby is running flash lite, so it would have to be ported or something, but j/w if this is something that could work out.