i forgot to mention something about compression. you can use flac or shn to loslessly compress your music. there are plugins for winamp (among other players) that support these formats... and everything you need is free!
FALC:
http://flac.sourceforge.net/
SHN:
http://www.etree.org/mkw.html
FALC:
http://flac.sourceforge.net/
SHN:
http://www.etree.org/mkw.html