Yes that is a good insight. I'll rephrase it to perhaps make it clear to a somewhat different set of people. If your strategy is to have a good median outcome of your life, you will still get to bet on longshots with high payoffs, as long as you expect to be offered a lot of those bets. The fewer bets you expect to be offered of a certain type, the more likely winning must be for you to take it, even if the "expected" pay out on these is very high.
A quantification of this concept in somewhat simple cases was done by Jim Kelly and is called the Kelly Criterion. Kelly asked a question: given you have finite wealth, how do you decide how much to bet on a given offered bet in order to maximize the rate at whcih your expected wealth grows? Kelly's criterion, if followed, also has the side-effect of insuring you never go completely broke, but in a world of minimum bet sizes, you might go broke enough to not be allowed to play anymore.
Of course, all betting strategies, where you are betting against other presumed rational actors, require you to be smarter, or at least more correct thant the people you are betting against, in order to allow you to win. In Kelly's calculation, the size of your bet depends on both the offered odds and the "true" odds. So how do you determine the true odds? Well that is left as an exercise for the reader!
And so it goes with Pascal's muggings. As far as my study has taken me, I know of no way to reliably estimate whether the outcomes in offered in Pascal's muggings are one in a million, one in a google, one in a googleplex, or one in 3^^^3. And yet the "correct" amount to bet using the Kelly criterion will vary by as big a factor as those probability estimates vary one from the other.
There is also the result that well-known cognitive biases will cause you to get infinitesimal probabilities wrong by many orders of magnitude, without properly estimating your probable error on them. For any given problem, there is some probability estimate below which all further attempts to refine the estimate are in the noise: the probability is "essentially zero." But all the bang in constantly revisiting these scenarios comes from the human biases that allow us to think that because we can state a number like 1 in a million or 1 in a google or 1 in 3^^^3 that we must be able to use it meaningfully in some probabilistic calculation.
If you are of the bent that hypotheses such as the utility of small probabilities should be empirically checked before you start believing the results of these calculations, it may take a few lifetimes of the universe (or perhaps a google lifetimes of the universe) before you have enough evidence to determine whether a calculation involving a number like 1 in a google means anything at all.
Googol. Likewise, googolplex.
The idea is to compare not the results of actions, but the results of decision algorithms. The question that the agent should ask itself is thus:
"Suppose everyone1 who runs the same thinking procedure like me uses decision algorithm X. What utility would I get at the 50th percentile (not: what expected utility should I get), after my life is finished?"
Then, he should of course look for the X that maximizes this value.
Now, if you formulate a turing-complete "decision algorithm", this heads into an infinite loop. But suppose that "decision algorithm" is defined as a huge table for lots of different possible situations, and the appropriate outputs.
Let's see what results such a thing should give:
The reason why humans will intuitively decline to give money to the mugger might be similar: They imagine not the expected utility with both decisions, but the typical outcome of giving the mugger some money, versus declining to.
1I say this to make agents of the same type cooperate in prisoner-like dilemmas.