I'm a big fan of type checking in general, and Typescript is a great example of a type checker that allows you to statically define all the dynamic idioms that you'd normally use. But for various reasons, that just doesn't seem to have happened in the Python ecosystem. Instead, you can either write normal dynamic Python without types, or you can restrict yourself to a vaguely Java-like subset of Python with hard-to-use generics and confusing rules about forward references.
I wonder if it would have been better to have taken the Typescript approach and have Mypy and all its annotations developed as a separate language, rather than as part of the Python language, with the expectation that they could eventually be merged at some point. As it is, it feels like both sides have been very constrained: Mypy has struggled to innovate on expressive type-level syntax because it only operates on standard Python code, and Python has struggled with balancing the various goals that different groups have for youry annotations.
The result is a kind of mess where it's still painful to type basic things like generics (yes, that's changing, but not if you need to support older Python versions), but you also have weird syntax that requires type annotations, even if they're meaningless (like with dataclasses).
I don’t understand what you’re getting at, but clearly you’re expressing some pain here: what are some examples?