In my opinion the sheer volume of "close enough" choices is what ruins Python's type system.
It's "close enough" to a usable type system that it's worth using, but it's full of so many edge cases and so many situations where they decided that it would be easier if they forced programmers to try and make reality match the type system rather than the type system match reality.
No wonder a lot of people in the comments here say they don't use it...
I think they can get away with the "close enough" solutions since Python's type annotations don't have any runtime contracts by default. Might be off-putting to people who are more familiar with statically typed languages (though not always, in my experience).
I would buy that argument more if Typescript didn't exist.
You can live with the "close enough" if you're writing a brand new greenfield project and you prevent anyone from ever checking in code mypy doesn't like and also don't use any libraries that mypy doesn't like (and also don't make web requests to APIs that return dictionary data that mypy doesn't like)
Retrofitting an existing project however is like eating glass.
It's "close enough" to a usable type system that it's worth using, but it's full of so many edge cases and so many situations where they decided that it would be easier if they forced programmers to try and make reality match the type system rather than the type system match reality.
No wonder a lot of people in the comments here say they don't use it...