This jives with my general reaction to the post, which was that the added complexity and difficulty of reasoning about the ranges actually made me feel less confident in the result of their example calculation. I liked the $50 result, you can tack on a plus or minus range but generally feel like you're about breakeven. On the other hand, "95% sure the real balance will fall into the -$60 to +$220 range" feels like it's creating a false sense of having more concrete information when you've really just added compounding uncertainties at every step (if we don't know that each one is definitely 95%, or the true min/max, we're just adding more guesses to be potentially wrong about). That's why I don't like the Drake equation, every step is just compounding wild-ass guesses, is it really producing a useful number?

It is producing a useful number. As more truly independent terms are added, error grows with the square root while the point estimation grows linearly. In the aggregate, the error makes up less of the point estimation.

This is the reason Fermi estimation works. You can test people on it, and almost universally they get more accurate with this method.

If you got less certain of the result in the example, that's probably a good thing. People are default overconfident with their estimated error bars.

I think the point is to create uncertainty, though, or to at least capture it. You mention tacking a plus/minus range to $50, but my suspicion is that people's expected plus/minus would be narrower than the actual - I think the primary value of the example is that it makes it clear there's a very real possibility of the outcome being negative, which I don't think most people would acknowledge when they got the initial positive result. The increased uncertainty and the decreased confidence in the result is a feature, not a bug.