I've had limited iPod exposure myself (rarely far from my computer, and my PDA gets the job done during those brief moments), but the Cnet article How to convert video for the iPod looks like a winner. The program they suggest, AVS Video Converter, can rip the video from DVD and make the conversion so there's no need for additional software. Of course any combination of DVD ripping and conversion (you ultimately want MOV format) would do.
Hope this helps,
Wife just got the new iPod 60 GB with all the bells and whistles. And it's supposed to play video. Is there a way to put DVDs on it. Not pirated, maybe a converter or something?