The Deal Or No Deal example is misleading if you are actually interested in discussing expected utility.
Dollars are not utility, a point which you usually seem familiar with except in producing your (unintentional, I hope) straw man:
If that first $20,000 is what I really want, the utility of higher sums may be much smaller than one might consider. So again, naively maximising expectation could leave one disappointed.
Naively maximizing expectation of what? You are naively maximizing expectation of dollars—this is not the same thing as naively maximizing expectation of utils. Concerns have been raised elsewhere, which I have not had a chance to look at in sufficient detail, about the latter—but your objection here clearly does not apply.
The Deal Or No Deal example is misleading if you are actually interested in discussing expected utility.
Dollars are not utility, a point which you usually seem familiar with except in producing your (unintentional, I hope) straw man:
Naively maximizing expectation of what? You are naively maximizing expectation of dollars—this is not the same thing as naively maximizing expectation of utils. Concerns have been raised elsewhere, which I have not had a chance to look at in sufficient detail, about the latter—but your objection here clearly does not apply.