I thought apple was allowing accessories to connect to the dock at the bottom after the 3.0 software update. Wouldn't it make more sense, and be sturdier if it was at the bottom? Also, with a bigger piece of hardware you might be able to use the quick pass functionality of some cards (the ones with ultra super secure RFID).
I think there is a licensing fee involved with using the dock connector - at the least you have to apply to Apple and all that.
There's no reason why you couldn't have a slide-in case designed to make this headphone jack-based one more sturdier though, or something along those lines.
Sure, but it won't work with any phone, because Apple uses a proprietary TRRS connector that allows data to be sent to the iPhone/iTouch (used by Apple for an external mic and remote on standard earphones).