Can't Update 1st-gen Shuffle

I have iTunes 7.0.2 and Mac OS X 10.4.8. My (1st-gen) shuffle is recognized and syncs older or non-DRM songs just fine, but won't sync some newer songs purchased through the iTunes Music Store. I get a message telling my to perform an update from the Summary tab.
Unfortunately, the Update and Restore buttons on the summary tab are disabled, so I can't use them. Nor can I use the iPod Updater 2.0.1 -- it never recognizes the iPod. The iPod Updater 2006-06-28 *does* recognize the iPod, but fails to recognize a software version. Likewise, the summary tab in iTunes says "n/a" for both Software Version and Serial Number. (I've tried "updating" using the 06-28 version; it tries, but gives me an error.)
How can I update this thing? I'd like to have my newer music on my iPod.

I downloaded and tried the Shuffle Reset Utility, but it couldn't restore the shuffle. I received an error message saying "No Firmware."
However, I went to my wife's Windows computer, downloaded the Shuffle reset utility, and it worked fine, there. In fact, the Shuffle worked flawlessly with Windows (I was able to sync it with my wife's iTunes library, etc).
I thought -- great, back in business! However, when I returned to the Mac and tried to sync with my own music library, I have the same problems; the Shuffle's version, serial number, et cetera isn't recognized, I can't sync newer songs, et cetera.
Obviously, the Shuffle isn't the problem. Also, the Shuffle worked fine with my Mac before the latest iTunes update; I'm beginning to think it's a Mac software issue with the update. The other possibility is a connection issue, but I've tried all the direct USB ports on the computer, and also a powered hub (also, the fact that the Shuffle worked fine, before, makes me think that the connection probably isn't the issue).
Dunno.

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