If you've got a new iPod and it freezes up when you try to send it songs from iTunes for Windows, it's probably not your iPod.
Karnak the Great says "Firewire." The question is "How is your iPod connected to the Windows machine?" Turns out there's a bug in the Windows XP IEEE 1394 driver (and an old one at that).
Wish I had found this out before I "restored" my iPod and wiped all the data. Like all old windows bugs, it's patched. Too bad the patch isn't distributed through software upate. No big deal, really, nothing lost but time.
On the good side, I've used Anapod Explorer a bit more. The lack of iTunes database integration is irritating, but other than that it's excellent.
I've also transferred a few discs off the iPod back on to the Mac, and PodWorks is pretty slick. The "Show only songs not in iTunes" filter makes it really easy to figure out what needs to be transferred, and "Send selected songs to iTunes" automates the import process.