I think the issues you encountered may be due to the specific libraries. Lots of the pre-typing libraries haven’t adopted static typing, like Django and Celery and then when your project is 95% Django and Celery you’re SOL.

I’m not even sure it’s possible to have Django typed without reworking the ORM, I’m thinking about reverse relations, .annotate(), etc.

Yes, there are type stubs for these libraries but they’re either forced to be more strict, preventing use of dynamism, or opt for being less strict but allowing you to use all the library features, at the cost of safety.

I think in the end, new libraries built with static typing in mind, like Pydantic, FastAPI, and Edgedb, are the answer.

There are type stubs for Django that somewhat avoid these compromises: https://github.com/typeddjango/django-stubs

To be able to do this they have to use a Mypy plugin though. And even then it's still far from perfect.