IPod Shuffle will not sync music - "files not available"

I originally thought at first I had a defective Shuffle. I returned the Shuffle and exchanged it for a new one and I am having the same problem. I also have already done a restore and software update to the new Shuffle and it did not solve the problem.
I connect the new Shuffle and iTunes goes thru the device setup just fine. When I go to sync music to the Shuffle, a box pops up stating that the songs could not be found in the library and cannot be transferred to the Shuffle. iTunes also shows all the files as missing when I select a song. Then a Windows pop up box states that the data on the hard drive where my music is stored has been deleted and cannot be restored. Needless to say the first time I read this I was freaking out because when I click on the drive it shows as totally empty. No files what so ever.
I then rebooted my computer and the drive and all of the files show up and everything is fine. iTunes works and can play files normally. I plug in the Shuffle and the same thing happens again.
I also have an Apple TV, 3 Nano's, and an iPod Touch that all work and sync just fine.

One song out of the album? Are you only syncing a single album to the iPod?
How is your iPod configured to sync? In other words, is it set to sync you entire library? Are you syncing specific playlists? Specific artists or albums? Are you auto-syncing or manually managing your iPod?
Patrick

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Message Edited by smaragd on 16-Dec-2008 08:35 AM

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Here is a screenshot of what I am talking about.
[IMG]http://i44.tinypic.com/34447pf.jpg[/IMG]
Here is the URL if the above photo doesn't show:
http://tinypic.com/r/34447pf/5
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