Can't add music. Can't restore. Error messages galore.

A few weeks ago my husband plugged in his iPod Classic 160GB into my iBook. It began to sync music, as per usual. After a short time there was an error message basically saying it couldn't sync "cannot create/read/write" or something to that effect (says my husband who is driving me up the wall for weeks about this but won't post here and ask for help).
There are other messages that (he says) say things such as "disc cannot be found" and another saying "file is being used/busy", also getting "cannot restore iPod/files not found", and a plethora of related messages. We own three other iPod's which are used with the same iBook (nano and shuffle's). All three sync, and are working, perfectly fine.
It was not dropped. Not exposed to harsh elements. It has not suffered any physical damage. Please, please, please help, if you can. Thank you.
* He just decided to share with me he has tried resetting it many times and received error messages on those attempts.
Tried restore and after an hour into synching error messages would begin and only 1/3 of the music would be on the iPod.
Tried enabling disc use, same error messages.
Tried the suggestion of plugging another device in an open USB port while trying to sync, still error messages.

Why not? We would need to know what you mean in order to help you....
Cheers,
GB

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