Well, the fair use laws might permit him to repurpose his video, however, as Dwayne points out the DCMA gets in the way.
I covered this topic in a business law class I took a few years ago when I went paperless for 8 weeks, which meant that I had to scan my books. I posed a similar question: Is it legal to scan your books to read on a tablet PC? It was a busy thread with may comments and even more off-blog emails traded. Ultimately, and after much research, I concluded that the fair use laws would permit this for personal use and I presented my research to my class in a presentation called, Wallpaper, Toilet paper, or ePaper.
But my research only addressed fair use of paper/books, not media. What Dwayne needs is a different kind of presentation.
Fortunately, I have one.
The clever and creative folks at Stanford University, in collaboration with Professor Lawrence Lessig, have recruited help from a few Disney characters to explain why Dwight can't legally record his DVDs to his iPod for personal viewing.
Watch the video.