ITunes not syncing music

Hello,
I am having a problem with iTunes not syncing music to my iPad. I want to have my entire library on my iPad, this used to fit.
A few weeks ago I started getting an error, most of my music had vanished. I attempted to sync it back, but was told that there was not enough space on my iPad, despite no new files being added.I looked again and noticed something. I had 20GB of OTHER in iTunes, this is approximately the size of my music library.
It is fairly clear what happened, the music files were corrupted somehow, but were still there and taking up space on the iPad. So I decided to restore my iPad. First restoring and once everything had been wiped and back to factory setting, restoring from a backup.
This worked and I was left with only 1gb of other. At this point there was still no music on my device sync music was unchecked.
So once I was sure everything was up and running, I checked the sync music box... and nothing happened. It would begin synching, it would determine the tracks to sync for a moment... then it would quickly finish syncing without adding the music files.
Does anyone have any ideas?

Have you authorized your new computer: Store>Authorize this Computer?

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