BBK,
First, congrats on the Mac purchase - you'll be quite happy with it
Now the fun part, thanks to the DMCA its illegal for me to tell you about solutions like MacTheRipper. Its illegal for me to say that MTR works (from what I hear), and the new 3.0b is even better (again, rumors)... The problem, from what I'm told, is that they charge for access to the site where you download the 3.0b which many people find intrinsically rude and some might even turn to other sites to find it.
But, like I said, thanks to the DMCA its illegal for me as a US citizen to tell you how to circumvent the copy protection on DVDs....which is a bummer because it also means I cannot share with you the program VisualHub ($20) which has a "rip to iTunes" feature ...
Of course, on the windows side, its been illegal for quite a while to discuss DVDShrink, so I guess we can't talk about DVDShrink either.
You mentioned that you had some MP4 files that you were trying to add to iTunes, assuming those are video files of legal content then this link might be helpful:
http://www.podcastingnews.com/articl..._for_iPod.html