simple answer but you'd be surprised how often it actually works ;-) lol
don't have an ipod so can't help too much on this one, don't they just show up as an external drive though so you can just drag & drop files onto them?
Had this with a mates ipod. He found he had to plug it into his usb port before opening itunes or it would'nt search for and find it if he connected it when he already had itunes open.
Reinstall iTunes, make sure you've got the lastest update. Also your iPod might need to be configured to use Windows, this will require you to format it!
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