ITunes won't sync music to my iPad

iTunes won't transfer all the music from my computer to my iPad. The sync starts, it transfers about 500 of 2500 songs, then just stops.
I have tried disconnecting wifi, reinitialising the iPad and practically every other tip I could find on this forum: no joy.
Just seems incredible that the music I have (mostly) paid for on iTunes won't sync from one device to another. Are Apple trying to get me to pay for iTunes Match?!
Thanks in advance for your help...

I don't use and never have usediTunes Match, I almost never buy music from iTunes, and I can sync all of music just fine - purchase and imported from CD's.
Have you tried syncing with the cable if you are using WiFi? Do you have enough storage space on the iPad? Could it be that the sync stops in the same place very time indication a corrupt song or album? Have you tried syncing the music in bits and pieces - simply as a troubleshooting step?

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