It is a little complex, first you use DVD Decrypter to copy DVD to Vob format, then convert it to iPod video.
All of these to convert DVD into one iPod video, I only use a Wondershare DVD Ripper to convert DVD and merge them into one file. It could help you convert any DVD(protected DVDs) to all popular video formats with only three steps. Also it let you set the movie effects.
You can free download it here: http://www.dvdvideosoftware.org/wondershare-dvd-ripper-platinum-for-windows.html


