I bought an iPod for Windows a couple of months ago and had tons of problems with the software and drivers - error messages that kept popping up on the screen and wouldn't stop until you turned the PC off, that kind of thing.
I returned it and bought an Archos, which I love. It isn't as sexy, true. But it is reliable, has great battery life, and a great community who have written their own open-source firmware that adds features not present from the factory.
-alan in seattle