There have been studies that asked people to make bets. Here's an example. It makes no difference -- subjects still arrive at fallacious conclusions. That study also goes some way towards answering your concern about ambiguity in the question. The conjunction fallacy is a pretty robust phenomenon.
I've just read the example beyond it's abstract. Typical psychology: the actual finding was that there were fewer errors with the bet (even though the expected winning was very tiny, and the sample sizes were small so the difference was only marginally significant), and also approximately half of the questions were answered correctly, and the high prevalence of "conjunction fallacy" was attained by considering at least one error over many questions.
Another month has passed and here is a new rationality quotes thread. The usual rules are: