One of my readers Rusen pointed to another very interesting (if somewhat specialized) book which deals with quantifying extreme or once-in-a-hundred-years events. The name of this book is "Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets" by Nassim Nicholas Taleb.
Taleb talks about events that occur at the extreme end of a probability distribution, where we think our models work but they models break down (because of a number of reasons). Taleb presents a perspective around where we should depend on models and where our intuition should tell us not to trust the models.
If readers want a preview of what's there in the book, check out this website www.fooledbyrandomness.com. (Taleb is releasing a second book this month called "The Black Swan: the impact of the highly improbable".)