Syncing stops midway through process

New iPod Nano, 5th Gen for Christmas, latest version of iTunes...
I'll start to sync and everything will seem to go fine... "syncing song 1 of 320" or something to that extent, but (long) before it finishes all of the songs. If I hit the sync button again, it'll start up again- usually continuing where it left off, but will once again stop early.
For me to bring over my full music collection, I have to sit there for an hour each time constantly watching and hitting the synch button repeatedly each time it stops.
Ideas?

Is this Mac or Windows?
i

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