> a lot of things with lots of experts and powerful institutions around them - that simply do not work.
Part of what's going on is that "does not work" is usually a vague moving target.
"Does not work" can be said about any gap between the goal and where we are currently. If you have a system that, on average, closes that gap over time, then the system "does not work" for the entire time it's running. After all there's a still a gap.
Chesterton’s Fence is a kind of inverse impulse to what you're describing. It may be that we think our current systems are nonsensical, but when we change them we realize we've created new problems that the old systems were solving.
And then there's often disagreement about what the goal should be. He mentions decreasing the amount of crime by how we handle criminals. Not everyone agrees that's the goal of the criminal system. Some people very strongly believe that criminals need to be punished or harmed, and those people vote. But punishment and crime reduction are different goals and they may compete. A solution that reduces crime may not harm criminals enough for the blood thirsty voters, and vice versa.
So my reading on all this is that, yes we have gaps in our understandings of a lot of things. But many of those will not be fixed until there's more agreement about what the goals are.