I thought, if outcome A is not more preferred than outcome B, and outcome B is not more preferred than outcome A, then of course the decision maker is indifferent between both outcomes, right? But if that's the case, the decision maker should be able to just flip a coin to decide. Not only that, but adding even a tiny amount of extra value to one of the outcomes should always make that outcome be preferred. So why can't a human decision maker just make up their mind about their preferences between "incomparable" outcomes until they're forced to choose between them? Also, if a human decision maker is really indifferent between both outcomes, then they should be able to know that ahead of time and have a plan for deciding, such as flipping a coin. And, if they're really indifferent between both outcomes, then they should not be regretting and/or doubting their decision before an outcome even occurs regardless of which act they choose. Right?

There are some very interesting ideas in the rest of this topic; I'm going to come at it from a bit of a different angle.

I think a lot of the indecision/doubt/regret comes from uncertainty. Decision problems usually have the options and payoffs mapped explicitly, but for real decisions we often have to estimate, without any rigorous way to do so. And our estimates are not just inaccurate, but also imprecise: it can be really hard to tell the difference between perfect indifference, slightly favoring A, and slightly favoring B.

On this view, the "waffling between incomparable outcomes" can be interpreted as "attempting to resolve severe uncertainty" - trying to get the EV calculation nailed down, before you can shut up and multiply.