"Oh, look, Eliezer is overconfident because he believes in many-worlds."
I can agree that this is absolutely nonsensical reasoning. The correct reason to believe Eliezer is overconfident is because he's a human being, and the prior that any given human is overconfident is extremely large.
One might propose heuristics to determine whether person X is more or less overconfident, but "X disagrees strongly with me personally on this controversial issue, therefore he is overconfident" (or stupid or ignorant) is the exact type of flawed reasoning that comes from self-serving biases.
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if you manage to get yourself stuck in an advanced rut, dutifully playing Devil's Advocate won't get you out of it.
It's not a binary either/or proposition, but a spectrum; you can be in a sufficiently shallow rut that a mechanical rule of "when reasoning, search for evidence against the proposition you're currently leaning towards" might rescue you in a situation where you would otherwise fail to come to the correct conclusion. That said, yes, it would indeed be preferable to conduct the search because you actually have "true doubt" and lack overconfidence, rather than by rote, and rather than for the odd reasons that Michael Rose gives.
Dad was an avid skeptic and Martin Gardner / James Randi fan, as well as being an Orthodox Jew. Let that be a lesson on the anti-healing power of compartmentalization
Why do you think that, if he had not compartmentalized, he would have rejected Orthodox Judaism, rather than rejecting skepticism?