I am not a fan of Taleb these days (he went off the deep end in conspiracy land), but it's worth reading his "Black Swan" book.

These tail risks are impossible to predict, and volatility of volatility of these events is incredibly high. So your expected value is better to think of as a "very broad range with a positive mean" - are you comfortable with this?

If you have infinite capital, and the market is infinitely liquid, sure. c.f. martingale betting strategies.

In the long run, we're all dead...