How about including a analog joystick VERY similar to the one offered on the PSP? It would be on the wrong side, but most buttons are programmable anyways, and you could get used to buttons on the right and left, with the analog joystick on the right.
On the bottom is the analog joystick (it works very well, and even for longer periods of time without fatiguing your fingers):
Very good idea overall! I love the idea of attaching to the top and leaving it there. have you thought about possible CF/SD passthrough slots? Or I guess you could just plug those in first and then the gamepad. Just remember to make it in the $30 price range, and not the ridiculous $100 like that bluetooth gamepad.