Apple Watch Will Not Sync Entire Playlist

Using a Series 2 Apple watch with iPhone 7. When I sync a music playlist to the watch only about 1 in every 10 songs will actually sync. The remainder of the playlist stays grayed out on the watch. The playlist is about 100 songs in length. I have the watch set to sync up to 250 songs. The playlist contains only songs that I have previously purchased on iTunes. I have recently discovered that if I go back to iTunes and re purchase the song - then that particular song will then sync to the watch. I obviously do not want to have to do this for an entire playlist.

Is this a bug or anything someone else has experienced?

Thanks in advance.