The probability question is straightforward, and is indeed about a 1000/1001 chance of tropical paradise. If this does not make sense, feel free to ask about it,
To me, this seems to neglect the prospect of someone else simulating the exact scene a bunch more times, somewhere out in time and space. To me, once you've cut yourself loose of Occam's Razor/Kolmogorov Complexity and started assigning probabilities as frequencies throughout a space-time continuum in which identical subjective agent-moments occur multiply, you have long since left behind Cox's Theorem and the use of probability to reason over limited information.
this seems to neglect the prospect of someone else simulating the exact scene a bunch more times, somewhere out in time and space
This is true - and I do think the probability of this is negligible. Additional simulations of our universe wouldn't change the probabilities - you'd need the simulator to interfere in a very specific way that seems unlikely to me.
...once you've cut yourself loose of Occam's Razor/Kolmogorov Complexity and started assigning probabilities as frequencies throughout a space-time continuum in which identical subjective agent-moment
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When preferences are selfless, anthropic problems are easily solved by a change of perspective. For example, if we do a Sleeping Beauty experiment for charity, all Sleeping Beauty has to do is follow the strategy that, from the charity's perspective, gets them the most money. This turns out to be an easy problem to solve, because the answer doesn't depend on Sleeping Beauty's subjective perception.
But selfish preferences - like being at a comfortable temperature, eating a candy bar, or going skydiving - are trickier, because they do rely on the agent's subjective experience. This trickiness really shines through when there are actions that can change the number of copies. For recent posts about these sorts of situations, see Pallas' sim game and Jan_Ryzmkowski's tropical paradise. I'm going to propose a model that makes answering these sorts of questions almost as easy as playing for charity.
To quote Jan's problem: