Take a look at AnyDVD + CloneDVD mobile. They aren't free but out of all the software I've ever tried for this purpose, in my opinion it's by far the best.
http://www.slysoft.com (also get it quick before they massively raise the price in the new year)
Comments
You need a dvd decrypter and an ipod converter. I use it and it's really easy to use. I'll find the thread and post the link.....
http://www.digitalspy.co.uk/forums/showthread.php?t=689464
http://www.slysoft.com (also get it quick before they massively raise the price in the new year)