I recall reading this before but reread and did some thought on it again. We may have a sort of a trade off here. I think I agree on Devil's Advocacy might be risky for the person doing it but I see obvious benefits in having one or two in a group as it emulates some of the epistemic benefits of value diversity as well as signals to the group that its beliefs shouldn't be taken that seriously.

You, dear reader, are probably a sophisticated enough reasoner that if you manage to get yourself stuck in an advanced rut, dutifully playing Devil's Advocate won't get you out of it. You'll just subconsciously avoid any Devil's arguments that make you genuinely nervous, and then congratulate yourself for doing your duty. People at this level need stronger medicine. (So far I've only covered medium-strength medicine.)

This is the major problem I see with my view that I'm unsure how to resolve though. Devil's Advocates may in practice be merely straw men generators.

Added: Brandon argues that Devil's Advocacy] is most importantly a social rather than individual process, which aspect I confess I wasn't thinking about.

Interesting I suppose I agree with it.