How much storage does that iTunes have? Most newer movies are > 4.7GB in size. Does the iTunes allow you to upload ISO or DOB files (files made from "ripping" DVDs?).
Note, in the USA, this is legal as long as you own the DVD (as opposed to ripping from a rental DVD), depending on the interpreration of digital media rights, when making a video as opposed to copying a DVD (making a DVD copy violates the reverse engineering of digital protection, although the programs that do this simply remove the protection, so it's not clear if a user of such a program is "reverse" engineering, as opposed to the authors of such programs).
Again, in the USA, based on the "Sony" case about recording programs with VCR's, if you played a DVD you owned on your TV and recorded it with a camcorder it would be legal. In fact the FCC shot down an attempt by a company Sony owned about not allowing DVR's to ouput broadcast video onto the firewire ports, citing Sony's previous court case where Sony fought for the right to record broadcast video.
Another option that wouldn't involve reverse engineering digtial protection would be to simply play the DVD on your computer, and use HyperCam II (do a web search) which records a user selected window and sound from the desktop. Fraps will do a similar capture but normally it only works with full screen, 3D output as with games.