Raven, Rip the DVD to your drive saved as a .vob (Mac, MactheRipper)
Then convert the .vob to mp4 (Mac, Handbrake)
Then get quicktime Pro 7, EXPORT the movie as m4v
Load it into your ipod
This method compresses it from say 7gb ripped to 500mp as ipod ready.
On a PC look for apps that export/import these file extensions.