You may want to give the Video converter in DVD Catalyst / PocketDVD3 a try. A free full 5day trial can be found here just to see if it will work for you
http://tinyurl.com/7vc5c It will convert .mov,mp4 plus it even has a iPod template built in but not sure if the DRM of iTunes would be a problem or not. I would try it myself but I will not buy anything that has DRM in it specially videos that I can record myself for free and that I have already paid for via a satellite subscription.