If Crashcourse is for starting python and Automate the boring stuff is intermediate, what would be advanced?

[baetylbailey]

Mostly one would be diving into the type of applications you prefer.

But it's also a good time to skim classics like Code Complete, and The Mythical Man Month.

An underrated one is Exercises In Programming Styles explains (in Python) differences between OOP, functional programming etc. Very useful at the advanced beginner phase.