Totally agree that the different failure modes are in reality interrelated and dependent. In fact, one ("necessary despot") is a consequence of trying to counter some of the others. I do feel that there's enough similarity between some of the failure modes at different sites that's it's worth trying to name them. The temporal dimension is also an interesting point. I actually went back and looked at some of the comments on Marginal Revolution posts years ago. They are pretty terrible today, but years ago they were quite good.
In principle, for work done for market, I guess you don't need to explicitly think about free trade. Rather, by everyone pursing their own interests ("how much money can I make doing this"?) they'll eventually end up specializing in their comparative advantage anyway. Though, with finite lifetime, you might want to think about it to short-circuit "eventually".
For stuff not done for market (like dividing up chores), I'd think there's more value in thinking about it explicitly. That's because there's no invisible hand naturally pushing people toward their comparative advantage so you're more likely to end up doing things inefficiently.
Thanks for pointing this out. I had trouble with the image formatting trying to post it here.
That's definitely the central insight! However, experimentally, I found that explanation alone was only useful for people who already understood Monty Hall pretty well. The extra steps (the "10 doors" step and the "Monty promising") seem to lose fewer people.
That being said, my guess is that most lesswrong-ites probably fall into the "already understood Monty Hall" category, so...