[stdbrouw]

> What are some well-known distributions that appear to have outliers? A log-normal distribution maybe?

All of them. Which is why outside of a handful of contexts, the consensus in statistical modeling nowadays seems to be not to worry about outliers unless the values are completely unreasonable or there are a suspicious amount of them.

As to your bootstrapping idea, why not bootstrap the entire distribution, why only the tails? If you only bootstrap the tails but allow draws from the entire empirical distribution then you are changing the underlying distribution.