I understand your point, but I'm not sure the analogy is quite correct. In the case of the lottery, where the probabilities are well known, to make a bad bet is just bad (even if chances goes your way).

In this case however, our estimated probabilities derive ultimately from our models of Eliezer in his authoring capacity. If Vladimir derives a lower probability than the one I derived on Harry using the solution I stated, and it ends up my theory is indeed correct, that is evidence that his model of Eliezer is worse than mine. So he should update his model accordingly, and indeed reconsider whether I was actually overconfident or not. (Ofcourse he may reach the conclusion that even with his updated model, I was still overconfident)