Downloaded iTunes music not sync'ing

I have a 4 year old 20Gig iPod (before the buttons were integrated on the scroll wheel) and have recently started puchasing music on iTunes...the songs that i've purchased are not transfered to the iPod b/c "you need to download the newest software for your iPod" so i did that ran the installation and the songs are still not copied to the iPod...any suggestions? current software:
OSX: 10.3.9
iTunes: 6.0.1
any suggestions?

It's not always obvious what causes the troubles, but after upgrading iTunes your iPod should be updated if necessary. I refer to the two articles I mentioned in my reply to Todd.
If your iPod doesn't respond, try resetting it:
http://docs.info.apple.com/article.html?artnum=61705
As a last resort you can restore the iPod, this will however delete all information on it.
http://docs.info.apple.com/article.html?artnum=60983
It's easy for me to speak, because I never encountered problems after upgrading iTunes from 4.9 to 5.0 to ect. up to 6.0.1
I have a 1st gen. 5 GB iPod, which still runs well (apart from the battery) and syncs with iTunes without troubles.
M

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