Some files won't sync

For some reason random files are not appearing on my iPod. I have enough space, I've tried restarting both the computer and the iPod, I've restored the iPod to an earlier date. Nothing seems to work!
The files are playable through iTunes on my computer, but they have exclamation points when I look at them through the iPod in iTunes.
I'm using the iTunes update, although I was having similar problems before that. The files are ones I own and did not buy through iTunes or other services.
The files playing in the window is the same file that is marked as 1a on the iPod in the attached picture.

File Sync Links that may help... all the links I have, since I don't know the cause of your specific problem
-https://forums.adobe.com/community/creative_cloud/host_sync
-http://helpx.adobe.com/creative-cloud/help/sync-settings.html
-http://helpx.adobe.com/creative-cloud/kb/arent-my-files-syncing.html
-Size Limits https://forums.adobe.com/thread/1488242
-sync and email link http://forums.adobe.com/thread/1427516?tstart=0
-Phantom folder problem https://forums.adobe.com/thread/1490445
-an overview of assets https://assets.adobe.com/files

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