I never understood why something like 4-pole 2.5mm phono wasn't used for USB. Then you'd have no orientation issues at all, and fumble-insertion would be trivia

I never understood why something like 4-pole 2.5mm phono wasn't used for USB. Then you'd have no orientation issues at all, and fumble-insertion would be trivial. An argument I've heard against this is that a rotating connector wouldn't be electrically stable enough. But this is easily addressed - you could easily add a toothed collar to the plug preventing it from rotating, at the small cost of there being a finite number of dozens of possible orientations, instead a continuous infinity. Or better, just design the protocol to be tolerant to packet loss.