IPod iTunes is up to date but my iPod wont update all songs???

The fact that Apple wants me to pay $50 for one incident...enough said! Sorry, I'm better now. So I have a legacy issue. iTunes version and iPod software versions are up to date but when I look at "My iPod" through iTunes it does not show all songs synced to my iPod?? Essentially my iPod is locked and grayed out and wont update new songs I have bought from iTunes. There is even a little lock at the bottom of the iTunes page "within" my iPod.... I cannot seem to unlock it and it is not because the iPod is physically on hold. Huge bummer - hugely annoying and Apple help desk wants $50 to tell me whats wrong with their product...

I've just started having a very similar issue. My iPod (20 GB dock connector, touch wheel with the four buttons above etc.) crashed for about the third time, wiped out all the songs on it and crashed iTunes each time I connected it to my Mac. In the past I have just loaded the iPod Updater again to re-install the software and start from scratch so I did this again. However, this is the first time I have done that after upgrading to iTunes 6 and I used an old iPod updater that I had previously downloaded (2005-03-23).
Everything seemed normal except none of the music I have purchased from iTunes will copy across to the iPod, error message = "some of the songs...were not copied..because your iPod software is too old. Go to...to get the latest iPod software update." I downloaded 2005-10-12 but it doesn't seem to do anything. Can anyone help?
With the updater I have just run the .dmg which opens the volume and then I've run the .mpkg. Do I need to do anything else?!?!?

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