Hi michael,
If you aren't able to get the looping option to work, here's another option...
There's an app that will do it for you… and its free!
LOOPYLOOPY
https://itunes.apple.com/us/app/loopyloopy/id435457141?mt=8
First connect your iPad to your computer. Open iTunes. Select your iPad in iTunes, and click the Apps tab. At the bottom you'll see File Sharing. Select LOOPY and click the "Add..." button at the bottom of the LOOPY documents window. Add the movie. Click the Sync button in the lower right corner. Open LOOPY on your iPad. Tap the Menu button in the lower right and select your movie.
There are some other apps (paid) that will do it for you like VideoLoop Playerhttps://itunes.apple.com/us/app/videoloop-player/id432855782?mt=8 and LoopVideoPlayer https://itunes.apple.com/us/app/loopvideoplayer-video-loop/id398897303?mt=8 so if LOOPYLOOPY isn't right for you then you could try the other two.
Hope this helps!
~Joe