I will say that the most issues I’ve encountered with Python happened on macOS machines. The default installation was always old, and success using a modern version depended highly on the techniques used to install it.

For anything that involves dependencies, I rely on venv or pyenv to create a clean environment. When on macOS, I tended to use docker/containers as well, but primarily because 99% of my Python work has been in a Linux environment and I wanted like-for-like as much as possible. But a good version manager directly on macOS should help quite a bit.