Puzzle 1: George mortgages his house to invest in lottery tickets. He wins and becomes a millionaire. Did he make a good choice?

This looks like a tree-falls-in-forest-did-it-make-a-sound question. The expected value was negative, the outcome was positive, "good choice" can mean either assessment, distinguish them, mystery dissolved.

‘expected value’ is typically defined in reference to a specific set of information and intelligence rather than an objective truth about the world.

Expected value is subjectively objective. It depends on the knowledge one has, but what knowledge one has is also an objective fact about the world.

After all, if there is any sort of free will, perhaps we have the ability to make decisions that are sub-optimal by our expected value functions. Perhaps we commonly do so (else it wouldn’t be much in the sense of ‘free’ will.)

Is this Sartre's concept of free will as actions coming out of nowhere, free of all considerations of what would actually be a good idea, with suicide as the ultimate free act? Eliezer has provided the answer to the Problem of Free Will here.