I think this oneohaha wrote:RootlessAgrarian, check this one, it might help.
http://forums.winamp.com/showthread.php?t=374929
http://forums.winamp.com/showthread.php?t=302469
is actually the Rosetta Stone this looks like so much fun I will just have to try it, shuffled playlist or not.
[update] dang, that link is now outdated, and shoutcast no longer ships a server for OSX. just linux and 'doze. I do have a linux box sitting around idle, but life is short and I'd rather play ETS2 (and work on my camera modding) than set up my private radio station... giving up on shuffle play for now, but I still want it!