ITunes 5.0 won't transfer purchased music to iPod

Hi, I just upgraded both my iPod and iTunes to 5.0. Now when I update my iPod iTunes says it can't transfer some of my music because my iPod software is "too old," and to go to apple.com and upgrade.
Now I have re-upgraded my iPod software several times with the same upgrade just in case there was a problem with the install. I have also reset my iPod to factory settings just in case that did something and I have restarted my computer plenty. Regardless, none of the music that I have purchased from iTunes gets transferred to my iPod, and iTunes still says my iPod needs to be upgraded.
How do I fix this?
Thanks!

I had a similar frustrating problem of my iPod losing its songs on it and not syncing any new purchased songs to it from iTunes. I do have a solution folks !
The solution that worked for me:
I trashed the newest iPod updater 2005-9-26 from my Utilities folder and then updated with the 2005-6-26 version 2.3 again that was already in the folder. I do still have iTunes 5 so seems like it's either a big problem with the newest iPod updater (2005-9-26) or the combination of the newest iPod updater with iTunes 5.
In short, for things to get working correctly on your iPod again ... get rid of the new and in with the old .......I'm happy now, try it !
And to think that Apple told me I had to pay $49.95 good for only 5 days of trouble shooting advice on this problem .... highway robbery !
-- Debbie

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