If you want me to ruin this for you, look up Bertrand's Paradox and The Problem Of Priors.

I recently had to deal with this, ugh, I just pick a prior or two and see what the outcome looks like. I'm not sure we can calculate probability of success, but rather use probability to find losing ideas that should never be done.

Nice.

What are some good books to build this sort of perspective on Probability/Randomness/Chance?