Windows Wont Recognize

I'm updating my Dads iPod for him and for the first time ever, Windows/iTunes wont recognize it.
On the iPods display screen it says do not dissconnect so its not my USB ports nor the cable. Any ideas?
BTW, this is the iPod Color U2 version thing

This http://www.copytrans.net/helpcopytrans.php#22 is an interesting iPod detection problem check-list.

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