The mathematics behind probability and statistics is about as ripe for intuition as calculus and linear algebra. A lot of it really comes down to counting in probability (calculus/measure theory for the continuous case) and quantifying properties about probability distributions for statistics.

The really hard part is the modelling part, where you transform the problem to a mathematical statement and vice versa. It's very easy to misinterpret both the problem in terms of mathematics and the mathematical result in terms of the problem. All the wrong answers to brain teasers like the monty hall problem, the tuesday boy problem etc., are right answers to the wrong question.

Unfortunately, in education we do not seem to want to discuss the modelling part on equal terms with the theory. We seem to be okay with solving the entire problem, or solving just the theoretical part with no regards to the application, but expressing just the mathematical problem to be solved is never appreciated. In a calculus setting, this could be deriving the answer to some physical problem depends on the solution of some partial differential equation -- even if you do not have the tools to solve it outright.

My guess is that it's just easier to teach theory with clear cut answers. Modelling the real world is ambiguous and hard.