(I liked your post, but here's a sidenote...)

It bothers me that we keep talking about preferences without actually knowing what they are. I mean yes, in the VNM formulation a preference is something that causes you to choose one of two options, but we also know that to be insufficient as a definition. Humans have lots of different reasons for why they might choose A over B, and we'd need to know the exact reasons for each choice if we wanted to declare some choices as "losing" and some as "not losing". To use Eliezer's paraphrase, maybe the person in question really likes riding a taxi between those locations, and couldn't in fact use their money in any better way.

The natural objection to this is that in that case, the person isn't "really" optimizing for their location and being irrational about it, but is rather optimizing for spending a lot of time in the taxi and being rational about it. But 1) human brains are messy enough that it's unclear whether this distinction actually cuts reality at the joints; and 2) "you have to look deeper than just their actions in order to tell whether they're behaving rationally or not" was my very point.