IPod won't sync purchased tracks (.m4p files)

My iPod will no longer sync songs I purchased from the iTunes store. The albums do not appear anywhere, and playlists do not contain purchased tracks. I noticed this after the last iTunes update (the version that introduced full screen cover flow). Everything else is working - I can sync podcasts and music ripped from CD's.
There are several other changes in my iPod that I believe to be related;
* I can't update the version; instead a see message that "Only Macintosh-formatted iPods can be updated" (my iPod is Windows formatted but I now use it on my mac).
* I cannot restore, instead I see a message that my iPod cannot be found.
Does anyone know of a fix for these issues?
1.25 GHz 15" PowerBook G4   Mac OS X (10.4.9)   4G 40GB iPod Software: 3.1.1

I just had the idea to sync my iPod using USB, whereas I had been using Firewire. It worked! No errors during transfer and all of my tracks show up on the iPod. I was able to do "Restore" and now my iPod is Mac formatted, and the Update button is available.
I'm marking my question as answered, but after this experience, I still wonder about Apple's support for older iPods;
1) Has Apple dropped Firewire support from iTunes with the recent updates?
2) Does a windows-formatted-ipod-used-on-mac fall into a void that is not fully functional in iTunes?
1.25 GHz 15" PowerBook G4 Mac OS X (10.4.9)

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