Ok, things seems to be working out now. I had originally let the iPod run all the way down in the hope that this somehow would help with the langauge selection problem. However, that proved unnecessary to the fix I needed.
In any event, I hooked the iPod up to the laptop earlier today to (Successfully) resolve the language problem. I then let it run down again, and hooked it up to a different USB port. When it connected again, the laptop iTunes library now contained all of the songs downloaded from the desktop to iPod.
Not sure how that happened, but it's very cool nonetheless.
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