ITunes lost all of my purchased music, will not allow me to re-download

I recently lost all of my purchased music, around 180 songs, out of the blue. This was not a hardware issue with the underlying block device, as the only music affected were recently purchased music.
I have tried multiple times to redownload my purchased items only to find that the download all button becomes gray and nothing is actually re-downloaded. I have tried this on Windows and on my Mac (which i was working on moving my music to) with the same results. At one point it actually re-downloaded one song however none of my other purchased items were downloaded and the "download all" button went grey.....
I am running the latest OSX Lion and the latest iTunes 10.5.2
Any advice or tips would be greatly appreciated.
Thanks,
Mike

Your iPod is designed to sync only one iTunes library at a time.  If you try to sync it to a new library it will replace the contents that are currently on the iPod with the contents from the new library.
So what you'll need to do is copy all the content currently on your iPod to your new iTunes library first.  Then you can go ahead and restore it to factory settings and start syncing it all back over to your iPod from scratch.
See this older post from another forum member Zevoneer covering different methods available for copying content from your iPod back to your PC.
https://discussions.apple.com/thread/2452022?start=0&tstart=0
B-rock

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