Winamp & Shoutcast Forums - Copyright infringement

I am entertaining the possibility of running an internet broadcast via shoutcast. From reading through the forums it seems as though, for most of the broadcasters, the only financial responsibilty for which they are abiding comes as a product of just buying a CD and broadcasting it's songs. As a whole, should I really worry about paying royalties and seeking legal representation to run an internet broadcast. The underground music scene for my local area (TampaBay) is really lacking in accesseability (spelled wrong, I think)) and I would like to really give a viable solution for my local scene outside of a clearchannel based "pop-media" broadcast. I would like to do this in a way that would be able to withstand the risk of being shut down or held liable for some large fine. I just want to make accesseable underground music, but I want to do it right so that I may have a chance at lasting (atleast for a little while). I'm not so bad at sifting through the technical issues of running a broadcast, however the legal side of things is definately not my forte. Let me know.