Simple mans reply: Yes.

For your needs, it sounds like two instances of WINAMP wil need to be running (one for shoutcasting and one for evrything else) and you will need the advanced line-in plugin from the plugins section of the winamp website. Go to radio shack and get a stereo cable with headphone jacks on either end and loop the out to the in on your soundcard (some cards can do this by themselves, but not mine

). Also, it would be good for the shoutcasting winamp to use the null-output plugin (again from the plugins section), so you don't get feedback and so it will use less cpu cycles (if you have less than a 300mhz machine you probably can't do this anyway).
-=Cassidy=-