HT1386 iTunes not syncing all playlists?

When I sync my 5s with my Mac, the playlists are not updating or syncing.  Furthermore, some of the songs are not playing again.  I had this problem before and never really could figure out what fixed it.  It just began working again.  Now, however, I have tried updating the software, re-syncing multiple times and it still won't work.  I had edited some of my playlists and whenever I sync my phone, it adds the old playlist to the Mac and adds a "1" to the title of what should be the new and updated playlist.  I have even deleted the old, original playlists and it's still happening.  After doing that, I can't get one of the playlists back on the phone at all.
Anyone else with this experience?

That still doesn't work.  I've tried several times.  Some of my songs, which are not purchased songs by the way, but songs off of cds are also not playable now.
When I check the box to un-sync the music, then click apply, a sync starts and immediately the box unchecks itself and all the playlists repopulate on the Mac screen.  They aren't even being deleted from my phone either.

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