Purchased music on new computer/will not load on ipod

This problem has gone on for months now and I'm at my wits end. I have a 2nd PC which I have authorized. Windows 2000
Business Ed. When I connect my IPod, I cannot get the music I have recently purchased from itunes 7.0 to upload on my 60/Video IPod. Absolutely zero uploads. Any suggestions?
Thank you sincerely!
I may have to have a funeral for itunes.

I cannot get the music I have recently purchased from itunes 7.0 to upload on my 60/Video IPod.
try playing one of the songs for a few seconds in itunes. does itunes ask you to authorise? if so, and if you do, will the songs transfer to the ipod next time you try to sync?

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