IPod won't sync any of my purchased mucic

After restoring my iPod to factory settings it is not syncing any purchased music I have lost everything. Ant ideas? Thanks

Now I am really starting to get ******. Especially after just watching an Apple commercial claiming that their products just work out of the box.
I have tried everything on this page: http://docs.info.apple.com/article.html?artnum=300766. Including recreating my iTunes library, which wiped out my playlists and upon re-importing my music duplicated most of my songs. Just spent 3 hours deleting dups. Resynched to my BRAND NEW iPod (having restored it about 4 times now) and guess what? Still skips ONLY the music I purchased on iTunes. How freakin ironic, iTunes DRM preventing me from playing music I purchased on iTunes. And no response from APPLE COMPUTER CORP on this issue.
Starting to lose my faith in Apple. It seems like they are starting to act like Microsoft.

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