Have you tried selecting the music to sync instead of auto syncing?
When you connect the iPad to the computer - let it sync if you auto sync. After it syncs, click on your iPad on the left side under devices. Click on the music tab in the iTunes window on the right. Click on the sync music heading to select it. Then click on all of your albums, or playlists - or whatever you use to categorize the music. Then click on Apply in the lower right corner.
I figured out how to play greyed out music. Let me know if the following works for you:
1. On your iPad, select iTunes icon
2. Select " downloads" on lower right bottom of screen
3. Select " library" upper left corner of your screen
4. Select "more" lower right bottom of screen
5. Select "sharing", then " my library"
Music should now play in iTunes and your music icon. Try it and let me know.
It worked for me!