The autopilot problem seems to arise in the transition phase between the two pilots (the human and the machine). If just the human does the task, he remains sufficiently skilled to handle the emergency situations. Once the automation is powerful enough to handle all but the situations that even a fully-trained human wouldn’t even know how to handle, then the deskilling of the human just allows him to focus on more important tasks.
To take the example of self-driving cars: the first iterations might not know how to deal with, say, a differently-configured zone due to construction or some other hazard (correct me if I’m wrong, I don’t know much about self-driving car AI). So it’s important that the person in the driver’s seat can take over; if the person is blind, or drunk, or has never ever operated a car before, we have a problem. But I can imagine that at some point self-driving cars will handle almost any situation better than a person.
The ev-psych reason for the “strong leader” pattern is fitness variance in the competition between men. The leader (dominant male) would be able to impregnate a substantial proportion of the women in the tribe, while the least dominant males wouldn’t reproduce at all. So males are much more competitive because the prize for winning is very high (potentially hundreds of children), while the cost of losing is very low (for women, the fitness variance is smaller because of the limit on the number of pregnancies in theire lifetimes).
So it’s a prisoner’s dilemma where the defector has a huge advantage. If everyone is democratic about sharing their women and one person decides he wants to take them all, he wins and his genes spread.
There are also ev-psych reasons why dictators tend to be corrupted: when you have power, you want to use it to give the advantage to YOUR offspring (or your group maybe?). So even if you have noble intentions at first, there will be a tendency to hoard resources for yourself or others you consider as part of your group.