Ye it really boils down to what it is that u want from ur music player. If u want the accessibility of iTunes, there is no beating it, I believe. If u want the nice album-cover viewing, there r competitors (dunno which but google it). If u just want something to load/unload ur iPod/whatever to and simply throw music onto - Winamp’s ur thing. It’s super light and does everything in 2 clix. There used to be a special plugin called ml_ipod for portables support but now I think it’s built-in.
They haven’t updated Winamp in years but frankly I don’t see what else is needed. God, anything but that resource-hogging and pretentious iTunes.