the older ones won't charge via USB, that is if it originally came with firewire (sub-3G, and i think early 4th gen's) so if thats the case then i'd assume you just need to charge it.

AFTER you do that and it's connected and working all you have to do is open up explorer and copy the music folder to your computer... upon adding that folder to your library itunes will do the rest (sorting and such)