I think that this is a great idea. I often find myself ending a debate with someone important and rational without the sense that our disagreement has been made explicit, and without a good reason for why we still disagree.
I suspect that if we imposed a norm on LW that said: every time two people disagree, they have to write down, at the end, why they disagree, we would do better.
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I had the same idea of buying very risky investments. Intuitively, it seems that world-saving probability is superlinear in cash. But I think that the intuition is probably incorrect, though I'll have to rethink now that someone else has had it.
Another advantage of buying triple rollover tickets is that if you adhere to quantum immortality plus the belief that uFAI reliably kills the world, then you'll win the lottery in all the worlds that you care about.