I bought a first generation Ipod. The big pluses for me were size, hardware interface (wheel control...yes I like it), and file shuttle. More times than I can count I've used it with my windows laptop and firewire card to move files around (mostly oracle dump files).

That being said, to say it works with Windows is a bit of a stretch. I've had to hack around the fact that Apple prefers to make me wait for Windows compatible updates and then short sheets the functionality.

When Karma is available, I'll punt the Ipod to Ebay and never look back.