Since barring global disaster there will be massively more observers
in the future, why did you  find yourself born so early?  Surely your
probability of being born in the future (where there are far more
observers) was much much higher than your chances of being born so
early among a far smaller pool of observers?

Isn't there a major problem here with the word "you" here? To whom or what is it referring?

If it is asking "Why did you, Brent, a man born in the 20th century, find yourself born in the 20th century?", then the answer is obvious; it's like asking why is twelve twelve, and not a thousand. You're not picking a number randomly when you ask "Why is twelve twelve?" - you're picking twelve.

The target of your question (Brent) indeed lives at a time with a relatively small number of observers - if you want to talk about how things are in the future, maybe you should ask someone in the future...

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