Tell him to get a good quality firewire card (adaptec, for example). I've tried the ipod through usb 1 and 2 on several pc's and have about 60% success. Seems to be a factor of the usb bridge quality. Best success has been on pc clones with asus and intel mother boards, sony machines and pc laptops. Least success has been with Dell desktops. Never tried an HP, but my guess will be that their internal components will be of similar quality to a Dell.
Firewire all the way ... though the new iPods will be charged through both USB and Firewire.