I own a 30gb Classic and never use iTunes to manage my iPod anymore. I use a freeware program that was recommended by another TFPer (thanks, Cynthetiq) called
Floola. It's pretty basic. As Daniel suggested, there are loads of other programs out there that do the same thing.
I vote iPod, but that's because I love, love, love mine. I take it everywhere. Someday I want a larger Classic.