When I was trying to solve the koan I focused on a few interrelated subproblems of skill one. It seems like this sort of thinking is particularly useful for reminding yourself to consider the outside view and/or the difference between confidence levels inside and outside an argument.
Also, I think the koan left out something pretty important.
Under what circumstances, if any, is it harmful to consciously think of the distinction between the map and the territory - to visualize your thought bubble containing a belief, and a reality outside it, rather than just using your map to think about reality directly? How exactly does it hurt, on what sort of problem?

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It looks pretty solid for describing unbounded epistemic rationality. It's slightly iffier from a bounded instrumental perspective in that it probably imposes some mental cost to apply it and their are many circumstances were its not noticably helpful. There's also the matter of political situations and similar were its -arguably- good to be generally overconfident.