i used iPodRIP on my brother's 3G 20GB iPod and his IBM ThinkPad T42 - it did not work. the iPod attempted to sync with the iTunes library and then iPodRIP cleared the entire iPod. needless to say he was very frustrated and i felt awful since that was our method of recovering some of his lost music files. he's since resumed downloading.
i would go with anything other than iPodRIP.