Configured the iPod on our WinXP box at home, and I was right in my assumption that setting it up for Windows was the best way to make sure it would work with all the machines I use.
Found out I needed one more cable than I had. Ran over to the university bookstore when I got into work to pick up a second extra docking cable so I have one for my Mac at work, one for the WinXP machine at home, and a travel cable for my and kproche's laptops.
Downloaded and registered PodWorks so I could pull files from the iPod back on to the Mac. Cheap, sophisticated, and has what looks like great iTunes integration. We'll see how it does when I pull a few files off the Win box at home and try to transfer them to the Mac tomorrow.
Downloaded and registered Anapod Explorer so I could pull files from the iPod to my Windows machines. Kind of hated it for a little bit, and it has no iTunes integration, but I compared it to a few alternatives and it's head and shoulders above the others. None of the windows iPod utilities I could find had iTunes integration. I'm not thrilled with it, but it does what it does well, and it wasn't a waste of $25. Deleted all of the music from the laptop and just transferred back a few songs, and it worked.
Ordered an imp from SiK, and a TuneDok too ($10 cheaper than Fry's).
Still no cases designed to fit the new controls. I guess I can wait.
All in all, though, a satisfactory result ;)