You're the best Jeff! Not the OP but I was thinking of doing the same thing.

1) Go here and download Handbrake for the Mac:

http://handbrake.fr/downloads.php

2) Put a DVD into your Mac, launch Handbrake, choose "iPad" from Handbrake's presets. Rip the DVD.

3) Drag the resulting file to iTunes

4) Sync the movie to your iPad.

5) Repeat for each DVD you want to import. Expect to spend and hour or more per DVD.

To buy new movies, use iTunes to connect to the iTunes Store, find the movie you want and buy it. Download it to iTunes and sync with your iPad. Or, you use iTunes on the iPad to buy and download directly to the iPad. You can also download rentals, but rentals are deleted 24 hours after you start watching them.

You either have to buy the digital version or download the movie from iTunes. Unless someone else knows a way?

Real slowly, can someone explain this to me? I own DVDs. I have an apple computer, an iPad and an iTunes account. Can kiddo watch his DVDs on the airplane? (the apple website mentioned the iCloud and needing WiFi, which I don't think is available at 30,000 ft or while driving to grandma's house) I was hoping the portable DVD player could be obsolete, but now not certain that that's the case. And what if we want to buy new movies (without owning the DVD)? How's that work? Thanks!