Well DVDs can be anywhere from 2-6gigs, uncompressed onto your computer, so "uploading" it to iTunes?
I'm not much familiar with the program as it's a piece of shit.
But best would to use DVD Decrypter to rip the DVD Disc, then Divx converter and make it AVI or whatever file iPods run.
As said, Yes this is 100% possible, how you to it, well there are countless ways.