Hey man, listen with shoutcast and winamp what you need to do is get the dsp plugin for winamp and the shoutcast server so you can broadcast directly from your pc but you will need to get a static IP address from ISP or you could ( if you are internet savvy) download the DUC from http://www.no-ip.com and this will "hold" your internet connection.
The other alternative is ( well there's a few ) is that you can get windows media encoder and use some one like stream guys (http://www.streamguys.com) or if your isp has media server ( notated by the "mms"://) then you could stream to their server from your PC. Soundforge had a product out but I cannot remember the name of it off hand at the moment.

if you need more info mail me at bughead@hotmail.com