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Why can't I sync a playlist ???

Incredibly frustrated!

iTunes 11.1.3
OSX 10.6.8
iOS 7.04

I have two frequently used playlists, 'my top 100' and 'never played 100'. The first one syncs just fine. The second has not synced properly for a long time since upgrading to iOS7.

I've tried the forum suggestions, turned stuff on and off, reset, recreate, restart, etc.. not working.

The kicker is that I can sync the songs in the playlist and the playlist name shows up under the playlists section of iOS7 but when I press the name I get a 'No Content' message. All I want to do is pick my playlist and hit shuffle.

I have no idea what else I can do, if you have solved this problem please let me know how to fix it.