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I mean, it's not a paradox, but it loses predictiveness. I also don't agree with (a) and how it interacts with (b) because losses are unbounded on both sides and optional stopping is infinite for St. Petersburg? So I don't think you can have both (a) and (b).
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in practice nothing is infinite and you're never offered potentially infinitely many identical coinflips for all your money and if you instead restrict to finite reasonable conditions you end up with "small % of huge payoff" which can in fact be worth a lot!
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I guess the point here is that there is usually an explicit downside risk constraint in most basic portfolio optimization problems; not to mention there are usually leverage constraints, among many other things, which of course aren't captured by just vanilla EV.
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There are exceptions, obviously! Times when the downside risk is significant. But then you separately think about downside risk for it. To use something other than linear EV (or similarly sharpe adjusting for correlation with portfolio) would get you laughed out of the room.
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Very few trades will be big enough where you'll want any nonlinear considerations; I think probably something like 0.01%? And even on those 50% of what you talk about is linear EV (possibly divided by volatility), and the other 50% is risk limits.
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