Wait. Are you saying Apple is the Devil, if you're the devil's advocate?
Then allow me to be the devil's prosecutor:
1) All wire cables need shielding. You're assuming a digital signal will fail less often than analog due to strong RF interference. But since digital cables use wires too, they too will fail if the field is intense enough, probably at about the same point as analog does (just as digital TV tuners do). And I've *never* experienced interference from my analog cables.
2) You bought cables with crap connectors. Any decent analog cable has connectors that don't crackle or quit when the line is bent. (BTW, all earbuds are fine examples of such crap.)
3) Phones come with 1 or 2 rings, usually 2. If this leaves in deeply dismayed and contemplating suicide, switch to bluetooth now. Problem solved.
4) What's the point of encryption on headphones? The audio bleeding through your earpads is audible to anyone within 5 feet anyway. If this made sense, it'd be available via bluetooth now.
5) Digital connectors won't bypass the internal DAC. The market for external mobile DACs is so small, mobile DACs will remain internal and in-line... inescapably, alas.
6) Again, nobody wants an ultra thin phone, except Apple -- so they can sell more replacement phones after you break yours for the fourth time in a month.
And remember, a digital output signal will require active headphones with batteries to drive an external amp and noise cancelling DSP. Thus *all* mobile phones just got a lot more fragile and expensive, in ways that do NOT serve anyone but Wall Street analysts. It's they who are afraid that too small an excess of useless features will cause Apple's stock valuation to slip, thereby driving the entire board to jerk their knees in perfect synchrony with "Yankee Doodle Dandy" while waving incense and sprinkling rose water.