Well, getting into a car with your family is not inherently bad, so it's not a very good parallel... but if your overall point is that "expected value calculations do not retroactively lose mathematical validity because the world turned out a certain way", then that's definitely true.

I think that the "what if it all goes wrong" sort of comment is meant to trigger the response of "oh god... it was all for nothing! Nothing!!!". Which is silly, of course. We murdered all those people and made those children cry for the expected value of the plan. Complaining that the expected value of an action is not equal to the actual value of the outcome is a pretty elementary mistake.