Playlist will not sync

I'm working with a client who is syncing his iPod touch.  He's been adding music to this iPod consistently for the last two years, and today, his largest and most frequently play playlist will not sync. 
If you click on the device, the playlist appears to be there, but grayed out.  I have deleted all the songs added to the playlist since his last successful sync and moved them to another playlist (which is not being synced).  The content bar at the bottom of the sync screen appears to shoot up, indicating that it will sync all the playlists selected (a total of 4) but when sync completes, the content bars drops way down, and only the other three (smaller) playlists have synced.
Any suggestions?

I went into preferences, under sharing and denoted the playlists that I would like synced...
The Sharing prefs are for sharing the library/playlists with other computers. It has nothing to do with syncing.
What am I not doing correctly to manage my lists between units
You don't manage lists between units.
When I plug in the ipod for which I would like the playlist synced, the lists do not transfer?
Connect your iPod.
Select it in iTunes then click the Music tab.
Select *Sync selected playlistc* then tick the playlists you want to snyc to that iPod.
Do this for all iPods.

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