So I bought an extension cable only for it not to work. Appears those are verify finicky even for the expensive versions (~$30).

I was just about to pluck $100 down for a used ipod touch when I got to thinking. The only thing preventing the ipad from plugging in are those fingers that hold the iphone/touch in place. If I can remove those, I can dock the ipad. So that's what I did. Simple. Just have to remove about 6 screws from the bottom and wiggle the finger holder out the bottom.

Works perfectly. Now to unlock this bad boy.