The fundamental, unsolvable difficulty of making decisions with imperfect information seems to be often under analyzed. Are there any related fields that study this decision making difficulty?
I highly recommend "Probability Theory" by E.T. Jaynes. Don't be fooled by the generic title - the book is my Bible for reasoning with uncertainty.
> In my opinion, this book is a required read for anyone who wishes to understand precisely how the scientific worldview is, in a mathematically defensible sense, the best possible worldview, the one that lets us optimally use evidence to develop an interlocked Bayesian network of evidence supported beliefs that can change and evolve as the evidence is accumulated. It also shows the critical connections between physics and statistical mechanics and Shannon's theorem in computational information theory, laying the foundation for a fair bit of modern physics as it demonstrates that physical entropy and information entropy are very much one and the same thing, from a certain point of view.