Purchased Music NOT transferring from ITunes to IPod

AArgh. I have an older version of IPod (non-clickwheel) with the latest vesion of IPod Software (2.2) installed AND ITunes 6.0 AND I've repaired permissions, restarted, all the common troubleshooting actions taken place.
My Purchased from ITunes music is not transferring at all to my Ipod. At one point even though I had the latest software I would get a message saying my Ipod Software was out of date , but that's not true.
????

I am having the same problem, but I just got a new 4th generation 20GB because my old one died. So I tried transferring my library onto the new iPod and it won't transfer any of the songs that I bought on iTunes. The error message says that my software is too old, but I just updated it numerous times. What is going on!?!?

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