The problem (in my opinion) is that Python gives you the tools (and perhaps even encourages you) to write code that would benefit from typing.

It's perfectly feasible to write maintainable, well-designed code in a dynamic language. I've worked with some extremely robust and ergonomic Clojure codebases before, for example. However, in Clojure, the language pushes you into its own "pit of success".

Personally, I never feel that with Python.