Yes, you can use either the shoutcast plugin for winamp or use windows media encoder. My experience being with wme I can say that it is fairly easy. Just know how to handle getting around a firewall if you have one.
This server, are you trying to say that you're going to have an ESF server that plays rap music? Or is this like, a listencast server. I hope it's the latter, because.. who's going to download all that music just to get into a server?
hmm sounds pretty cool hope u get it working... oh and by the way if u do tell me... im might just put up a Techno/Trance/ Melodic Power Metal station up myself well Good luck with it and PM me if u get it working so maybe i can start my own