>What application do you use you manage your digital library? I used iTunes because I always figured I would get an iPod.

If you do any running, its hard to beat the Nano. 8 gigs, small and wafer thin, and the thumbwheel of course. And if you like Nike running shoes, the Nike/Nano shoe computer is a nice addition. Tracks your distance and pace (and tells you), history, best mile/km.