iPod can only support mpeg4 video,so you must make sure the video is mp4 format ,you need to have a 3rd party tool to help you to convert dvds and video into mp4 or h264 format, add them into itunes library, then sync to ipod.
Try Cucusoft ipod video converter,it support convert video to iPod directly. Some other software need two steps: 1. convert video to avi; 2. convert output avi to iPod. That solution wastes lots of your time. We need only one step, direct convert video DVD to iPod. So this converter speed is far faster than others
download at http://www.mp3dvdsoft.com/dvdtoipodconverter/index...
GOOD LUCK!