A few comments

[altaurog]

Thanks for compiling this list! I learned quite a lot here.

For static and runtime type checking, have you had a look at mypy and pydantic?

I didn’t follow the part about relative import not able to import from parent directory. If parent directory is also a python package, this certainly will work: from ..module import. Do you mean cannot import from a non-package? That would be true for non-relative imports as well.

On dependency hell - I have run into this, but very infrequently. I have also found that most of my python projects have significantly fewer dependencies that similar projects in other popular languages, perhaps because the standard library is rather comprehensive, and many of the high-quality libraries focus on maintaining zero or few dependencies.