I'd imagine that someone, or Apple, would make a little, very thin 'bracket' that just attaches from the standard dock, follows the contour of the iPad to the connector and connects as flush as possible.
I Steve won't go for it tho' since he's all about the minimalism when it comes to ports & buttons & such. How about one port on the back & a squarish dock that can be turned on it's side? I would draw ya a sketch but I failed art.....