TheOtherDave comments on Welcome to Less Wrong! (2012) - Less Wrong
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That's an excellent question. I haven't, but would be interested in exploring this if you have a preferred tool.
I've gotten some benefit when talking about complex issues from introducing formalisms such as labeling key entities and using those labels rather than vague pronouns, or being precise about "there exists an X" vs "for all X", and stuff like that. That said, there are signalling difficulties with doing that in most communities.
I've tried Rationale before (http://rationale.austhink.com/), but unfortunately it's not free. It's good at organising evidence and counter-evidence, teasing out premises, and trying to ground each one.
With larger arguments, it helps a lot in keeping track of all the parts -- better than writing. Where it fell down was in comparing the relative weight of different pieces of evidence, or in general handling uncertainty.
Mm. Not really interested in paying for the privilege at the moment.