I cannot download music purchased from iTunes store to iPod

All of a sudden when I connect my 2G Nano I get an error message that says, "Some of the items in the iTunes library were not copied to the iPod "your name iPod" Because your iPod software is too old. Go to the Summary in iPod preferences and click Update to get the latest iPod software update."
When I click OK The "Update" button is greyed out and I cannot select it. On the Summary tab under "Version" it says "your iPod is up to date."
What I noticed is that any songs in my playlists that were purchased through the iTunes music store were not transfered to the iPod. The difficult work around is to burn those songs to a CD and re-import them as mp3's. I tried deauthorizing and reauthorizing my computer which did not work. I also rebuilt my iTunes music library which did not work.
I belive when I irst set up this new iPod about 3 weeks ago this was not a problem and purchased songs transferred from iTunes to the iPod but now they don't.
Any Suggestions?

Also I forgot to mention that when all this was happening, I wanted to Retore my iPod but this option was also greyed out in the summary section and it wouldnt let me do it, therefore I hooked it up to my Windows XP machine and was able to restore the iPod. Now it was formatted for Windows. I hooked it up to my Mac machine and got all the same problems but it downloads everything from itunes to the iPod except purchased music.
So I opened iPod Updater and it said that it cannot update the iPod because it if formated for Windows. It also says if I now want to Restore it, I need to connect using a firewire cable whereas before I was using a USB cable because it said the Nano is not compatible with a firewire cable.
Arghhhh.

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