Excellent post. Let me know if this is in concert with your thinking: The more +EV a hand is, the less risky it is (as opposed to investing, where risk and return are usually positively correlated). However, where you can add EV, if you are willing to take on more risk/varaince, would be by playing marignal hands where you can win big/lose big (speculative hands like SC). People are who willing to tolerate more risk (greater bankroll swings) should play these hands, whereas those who like to keep varaince to a minimum should avoid them.

I wonder if these other correlaries b/w poker and investing work:

The "average" investor will sell a winning stock too early, and hold on to a losing stock too long. Or, in poker, the "average" player loses value on winning hands, and stays in losing hands too often.

Curiously, as an unrelated aside, why would we expect Art, Collectibles and Gems to have a higher expected return than, say, the US stock market? Greater risk is obvious, but shouldn't the utility that one gets from owning Art/Collectibles/Gems reduce the expected returns? (Almost like a continuous dividend).