My worst experiences universally have always been python projects.

Do you mind sharing why do you think this happens ? Although I never worked professionally with python, this sentiment matches with my experiences as a user. So I don't have a lot of context why this is the case.

Some siblings in this thread provided some explanations that mostly boils down to 'bad tooling' in one form or another. But this doesn't feel right.

In my opinion if it was just bad tooling this problem would be solved by now.