"You shouldn't find yourself distinguishing the winning choice from the reasonable choice."
I disagree. Let's say there's box A with $1000 dollars in it, and box B with $10,000 in it 1% of the time, and you can only pick one. If i pick A and my friend picks B, and they get the $10,000, they might say to me that I should wish I was like them. But I'll defend my choice as reasonable, even though it wasn't the winning choice that time.
I believe it should be read as:
In your example, your friend picked the choice that won once. It was luck, and he's happy, and all is well for him. However, the expected value of box B was $100, which does not win over $1000. Arguably, the gambling in itself may have nonzero utility value, and the certainty of obtaining $1000 may also have nonzero utility value, but that seems irrelevant in your example from the way it was formulated.
TL;DR: It seems like you're disagreeing more on the formulation or wording than the actual principle.
"You shouldn't find yourself distinguishing the winning choice from the reasonable choice."
I disagree. Let's say there's box A with $1000 dollars in it, and box B with $10,000 in it 1% of the time, and you can only pick one. If i pick A and my friend picks B, and they get the $10,000, they might say to me that I should wish I was like them. But I'll defend my choice as reasonable, even though it wasn't the winning choice that time.