Not garenteeing it will work and I can't look and see (not on windows) but DVDshrink will output to several different formats so check what your Ipod will play and see if you can match it.
Sometimes you need to use another program first, like AnyDVD, to get the DVD image from the disk, because it uses a protection mechanism that Handbrake can't get through.
Try this dvd to ipod converter:
http://www.tipard.com...o-ipod-converter.html
It can easily convert DVD to MP4, H.264 video formats and audio MP3, M4A and AAC without any loss quality of sound and image.
It also has strong editing functions of video trimming, video cropping, video joinning and video effecting. You can also capture your favorite pictures when you preview.
Hope it helpful for you.