I'd use Senuti, plug the iPod in, open Senuti, press Cmd-A, and press import on the upper right corner. The songs go right in iTunes, then you can Macify your iPod.
I don't know if this is the case or not, but you can transfer large files over a network or direct connect them with ethernet. It works Mac to Mac, so there is probably a Mac to PC compatibility. Just to throw out an idea if you have more than music to transfer.
(Maybe switch iPod to hard disk mode to transfer files.)
Comments
http://www.ilounge.com/index.php/art...d-to-computer/
=2 second google search.
(Maybe switch iPod to hard disk mode to transfer files.)