I've never tried that, and I'm curious as well to hear from those who have. I still need to figure out how to get my nano to delete files to be removed before it tries to add new files into the system. I often have to manually intervene when updating PodCasts.
Despite the grumbles about iTunes, this is the program that most of us must use with the iPods that most of us have (if we have a digital music player). So I thought it would be useful to have a thread to share useful tips & tricks for iTunes, our iPods, and maybe helping each other work through...