Playlist refuses to sync

First off, I have read all the other "failed to sync/greyed out playlist" help threads and none of the suggestions have seemed to help.
Now, the problem...  I purchased several albums off of Itunes last night, created several new playlists with the new purchases in them and then proceeded to sync the new playlists with my iPad wirelessly by simple drag-n-drop  All the playlist worked fine except for one, for the new Black Keys album, which was present on the iPad but was blank.  I then looked at the same playlist on iTunes and saw that it was greyed out and had a little icon next to all the songs I had never seen before,
After a couple of trys of erasing and creating new playlists on itunes the album was no longer greyed out and the symbol was gone, but now when transfering onto the ipad the playlist would still apear but be empty.  I then tried to manually sync the iPad from a fresh slate, getting rid of all the music and then syncing up manually.  Everything transfered except for the Black Keys playlist.
Please help, WTH is going on?

Just drag the album to the IPad.
No need for a playlist for an album.

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