I recall people being able to make a Windows iPod work on a Mac, but not vice versa. There is a topic on Apple's Discussions site on this subject. Search for "converting iPod from Mac to Windows XP".
One more thing. Be careful to not refer to your iPod as a "Click Wheel" iPod when selling it. That designation is left for the mini and the 4G. The buttons actually surround the wheel on your model, so, it's not the same.