"Still, I won't knock the guy for coming up with a proposal for something better than the unencrypted store-and-forward system we have now. It is all about convenience vs security, if we can get increased security for all, even if not perfect, it is better than what we have currently."
Unless it becomes LESS convenient, turning the average person OFF to the idea. I sometimes wonder if we're going to find it's an UNhappy medium out there: too irksome to use yet not secure enough to be practical. Remember the unwashed masses control the market, and they're searching for unicorns at this point. And we REALLY need the herd effect for this to be really effective. Unless, of course, the State has the computational resources to still winnow this out, in which case we're at the Big Brother stage already, in which case we're pretty much screwed.
"In seriousness though, the combined masochists and wimps are what? 5% of the population? more? Even if it was 25% (a bit optimistic I think), that leaves 75% that would be scared enough of the threat to reveal what is demanded, or they will give in not too long after the procedure has begun."
But like you said, natural selection might result in security people hiring sociopathic masochistic loners since they can't be tortured: directly (wrench turns them on) or indirectly (don't care about anyone else enough for that to be an angle). And this is only in SEMI-jest, since it seems sociopathy is just about a requirement for ANY position of power.