I do agree more people should read a few early Platonic dialogues because he teaches you to question things. I think, beyond anything else, that is what he wanted to teach. A lot of people call themselves skeptics today, but they seem primarily interested in debunking ideas and attitudes other people have that they don't share, but don't see that there is a lot of things they themselves take for granted.
Totally agree with your other statement.
His critique of democracy does absolutely have a few good points. A lot of people get really mad when they see it, but I don't think that is at all constructive. If democracy is a good idea, it must stand on its own legs. We can't counter its criticism with what it promises to deliver, but only the reality of what it delivers. Denying or attempting to conceal its problems makes addressing them that much harder, and which problems are easier to fix after having festered for a long time?
At the same time, I think the very Athenian democracy he criticized solved many of our problems today. Athenian officials had real skin in the game in a way ours do not. They risked ostracism (10 years of exile) if they misbehaved.
I'm afraid this is all a moot point because democracy has already disappeared in the U.S.. We're a democracy in name only. Hopefully we don't go the way of the DINOsaurs.