Having problems with syncing iPad from iTunes

I am trying to sync a playlist from my itunes to my ipad but every time i do, it won't upload onto my ipad. It actually takes music off. I don't know if i need to restore the ipad and resync the whole thing or if there is a way i can just get it to resync my music. When I go to the tab of "on this ipad" this is what i get I understand that the cirlces on the left of the songs are the songs that aren't available on my ipad but how to i re upload them??? every time i try to sync nothing happens at step 6 other then "waiting for changes to be made" and it finishes. i haven't seen any songs go onto my ipad. and everything is updated.
Please help.

I know that it is time consuming and a bit of a pain in the butt to have to do it, but I would backup the iPad, restore to factory settings and then restore from the backup, and sync everything back to the device. It's going to take a while because you have a ton of music on the iPad, but IMO, that would be your best option now.
You could try unsyncing all of the music, and then resync it all again, but that takes time as well. If you are going to spend that much time trying to fix it, you may as well restore the device ...IMO once again.
Use iTunes to restore your iOS device to factory settings

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