Purchased music not syncing from new macbook

So I had a powerbook g4, and recently purchased a new macbook, and firewired my PB to the macbook, and all data, apps, etc came off without a hitch. What I did notice however, is that all the music in my itunes that is purchased will no longer sync to my ipod classic. I've updated the ipod and itunes software. I can listen to and play the purchased songs on my macbook, but won't sync to ipod.
If I hook the ipod up to powerbook, the songs load right away, but I want to use my new macbook for managing all my music.
I've repaired permissions on my macbook 2x, but nothing works.

http://support.apple.com/kb/HT4527?viewlocale=en_US&locale=en_US

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