As a user of various python apps on windows I can tell that in practice it’s one of most confusing experience among all other languages. I have to purge everything python-related and reinstall it once a year.
If you are using apps that have been packaged with PyInstaller (or a number of other methods) for end-user use, I don't understand this: I use a number, and it's completely painless.
If you are using a systemwide Python installation and installing apps into it with pip, then, yes, that's potentially a world of needless pain.
If you are using a systemwide Python installation and installing apps into it with pip, then, yes, that's potentially a world of needless pain.