I think there's some value in that observation that "the all 45 thing makes it feel like a trick". I believe that's a big part of why this feels like a paradox.
If you have a box with the numbers "60" and "20" as described above, then I can see two main ways that you could interpret the numbers:
A: The number of coins in this box was drawn from a probability distribution with a mean of 60, and a range of 20.
B: The number of coins in this box was drawn from an unknown probability distribution. Our best estimate of the number of coins in this box is 60, based on certain information that we have available. We are certain that the actual value is within 20 gold coins of this.
With regards to understanding the example, and understanding how to apply the kind of Bayesian reasoning that the article recommends, it's important to understand that the example was based on B. And in real life, B describes situations that we're far more likely to encounter.
With regards to understanding human psychology, human biases, and why this feels like a paradox, it's important to understand that we instinctively tend towards "A". I don't know if all humans would tend to think in terms of A rather than B, but I suspect the bias applies widely amongst people who've studied any kind of formal probability. "A" is much closer to the kind of questions that would be set as exercises in a probability class.
The best laid schemes of mice and men
Go often askew,
And leave us nothing but grief and pain,
For promised joy!
- Robert Burns (translated)
Consider the following question:
Or, suppose Holden Karnofsky of charity-evaluator GiveWell has been presented with a complex analysis of why an intervention that reduces existential risks from artificial intelligence has astronomical expected value and is therefore the type of intervention that should receive marginal philanthropic dollars. Holden feels skeptical about this 'explicit estimated expected value' approach; is his skepticism justified?
Suppose you're a business executive considering n alternatives whose 'true' expected values are μ1, ..., μn. By 'true' expected value I mean the expected value you would calculate if you could devote unlimited time, money, and computational resources to making the expected value calculation.2 But you only have three months and $50,000 with which to produce the estimate, and this limited study produces estimated expected values for the alternatives V1, ..., Vn.
Of course, you choose the alternative i* that has the highest estimated expected value Vi*. You implement the chosen alternative, and get the realized value xi*.
Let's call the difference xi* - Vi* the 'postdecision surprise'.3 A positive surprise means your option brought about more value than your analysis predicted; a negative surprise means you were disappointed.
Assume, too kindly, that your estimates are unbiased. And suppose you use this decision procedure many times, for many different decisions, and your estimates are unbiased. It seems reasonable to expect that on average you will receive the estimated expected value of each decision you make in this way. Sometimes you'll be positively surprised, sometimes negatively surprised, but on average you should get the estimated expected value for each decision.
Alas, this is not so; your outcome will usually be worse than what you predicted, even if your estimate was unbiased!
Why?
This is "the optimizer's curse." See Smith & Winkler (2006) for the proof.
The Solution
The solution to the optimizer's curse is rather straightforward.
To return to our original question: Yes, some skepticism is justified when considering the option before you with the highest expected value. To minimize your prediction error, treat the results of your decision analysis as uncertain and use Bayes' Theorem to combine its results with an appropriate prior.
Notes
1 Smith & Winkler (2006).
2 Lindley et al. (1979) and Lindley (1986) talk about 'true' expected values in this way.
3 Following Harrison & March (1984).
4 Quote and (adapted) image from Russell & Norvig (2009), pp. 618-619.
5 Smith & Winkler (2006).
References
Harrison & March (1984). Decision making and postdecision surprises. Administrative Science Quarterly, 29: 26–42.
Lindley, Tversky, & Brown. 1979. On the reconciliation of probability assessments. Journal of the Royal Statistical Society, Series A, 142: 146–180.
Lindley (1986). The reconciliation of decision analyses. Operations Research, 34: 289–295.
Russell & Norvig (2009). Artificial Intelligence: A Modern Approach, Third Edition. Prentice Hall.
Smith & Winkler (2006). The optimizer's curse: Skepticism and postdecision surprise in decision analysis. Management Science, 52: 311-322.