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?
“it’s heartbreaking to just say no”
Sounds like a false dilemma; I would argue that, even if you accepted James Shikwati’s analysis (which I don’t), the first reaction should be to see whether it’s possible to enact more effective methods of assistance, rather than immediately give up.
“What does aid to Africa have in common with healthcare spending?”
I assume “they’re both politicized topics that smart people seem to disagree about” is not the answer you’re looking for.