Hard to say. Apple is often able to release new products at insane price points, but to reprice existing products is more dicey, especially when laptops are one of their most expensive products on offer. I think you have something of a point: Apple products are mostly aimed at people with lots of disposable income, but raising the price still reduces the total addressable market size. The only way to know is to run the experiment.

What Apple does is they make a new model or add a big feature to the latest model and drastically increase the price. You can see that with the iPhone X, the iPad Pro, and with the introduction of the retina macbook pro's, or even with the touchbars. Apple knows how to increase prices and keep the vast majority of their customer base.

You're right, but the iPhone X is well below the price point of their Macbook Pros (closer to Macbook Airs though). Their flexibility is reduced the higher the absolute price point goes. At a certain point, people really can't spend that money.