What are some good books to build this sort of perspective on Probability/Randomness/Chance?
I'll start with the easy one that was written in native English, William James's Pragmatism. Its only 4 hours long, and teaches 1 of the 3 branches of metaphilosophy(Pragmatic). For ROI in philosophy, it doesn't get better than this. It teaches one of the 3 theories of Truth.
Next is significantly more difficult, but everyone only understands 10% of Wittgenstein. Read both early and late Wittgenstein. If I remember correctly, its ~12 hours of pain as you will barely understand him. However, it shakes foundations of math and science as you will find these are mere constructs of language. This will also teach you 1 of the 3 branches of metaphilosophy(Analytical), and teach you how language works. You really need to read both early and late. But I imagine reading early Wittgenstein will convince you to read late. Its super painful, but you should deal with the pain.
(the remaining branch of philosophy is Continental... that takes a long time to learn, but its mostly nonsensical rebuttals to Plato, take it from someone who read this for 8 years...)
Regarding that initial thought on the Problem of Priors, here is a quick youtube video: https://www.youtube.com/watch?v=xy6xXEhbGa0
There is a lot here which jives with ancient Hindu Schools of Philosophy, specifically; Nyaya (https://en.wikipedia.org/wiki/Nyaya), Vaisheshika (https://en.wikipedia.org/wiki/Vaisheshika) and Charvaka (https://en.wikipedia.org/wiki/Charvaka).
Bayesian epistemology with priors have always been problematic since if there were no constraints on prior beliefs than anything goes. But in order to constrain the priors you need to know the distribution to calculate probabilities.
Stick to contemporary people who are dead and have no marketing team to promote them.
