You laid out a number of points there, and I think some of them are indicative of what's really holding back security for the masses.
"Matching a name with a social media is the wrong way to lookup others" -- this is the one I take greatest issue with, because it's the way we know people now. All the people I collaborate with online now, I know them by those exact names. Coworkers, remote collaborators, friends on instagram, famous software engineers (whose work I might want to consume), even my own brothers... I know them by a set of these identities. This is how I know people.
To illustrate this point: if my own brother wrote me a message and posted it simultaneously on Twitter, Facebook, and LinkedIn, I would think "yeah, that's my brother." Moreover, and more importantly, if he left those posts up publicly, over time the strength of my conviction that he actually wrote the messages (and it wasn't a short-term compromise) would grow.
This works even for people you've maybe never met in real life. If hacker news user "jashkenas" announces on HN that he has a new version of CoffeeScript, I expect that's him. If he pairs it with a tweet, then I really expect it's him. The fact that this method works for possible strangers and loved ones is very powerful. Remember, this isn't just about secure messaging. If someone doesn't have any such identities, then there's always still the fallback: exchange an identifier in person.
The alternatives are so nasty -- in person meeting, coordinating enterprisey apps, and so on -- we'll never get anywhere with this kind of thing. The solution I think you are suggesting requires a lot of human effort to figure out if you have the person you want. This is one of the danger points of PKI. And one of the inconvenience points.
"Leaving people to manage their own private keys is worse for security than having them managed by others." Part of me wonders if you're just trolling. I don't understand this, and I've read your paragraph a few times. There is the confusion argument - that people don't understand how to manage them, which is a problem we're tackling. Our argument is that it's possible to build something usable (finally!) where people do in fact own their own keys.
But you go on to say "software glitches" and "updates" are dangerous for individuals who have device keys, and then suggest they'd be ok if their enterprises / social networks managed their private keys for them. In this case, you're talking about expanding the threats considerably, while still leaving client apps that need to be updated and do the work.