Spartan301: firstly you need a copy of mactheripper.
http://www.mactheripper.org/ This allows you to rip dvd's onto the hard drive. you can select chapter by chapter. menu's, credits. Which regions for it to be formatted to should you copy it to another blank dvd ect.
You then need a converter. I use dvd re-master (you need pro, and can get a copy for about 20 pound from their site. the shareware version leaves a dvd in the bottom left of the screen so is pointless and merely to show you the kits capability should you buy it
http://www.metakine.com/products/dvdremaster/). It allows you to choose specifically to copy to either DVD or i-pod.
Once you have ripped the DVD onto the hard drive using mactheripper, and converted it to the i-pod format using DVD remaster.
Finally, you simply select 'import' through the file menu on i-tunes and copy it in and then onto your i-pod.....done