I think that https://github.com/microsoft/pyright/blob/main/docs/mypy-com... actually covers the majority of my gripes with mypy, the main issues I encounter with mypy are due to its lack of precision. It produces a lot of false positives for code that is well-typed that pyright can handle. Also the lack of type inference and lack of type checking for unannotated code (by default) is kinda painful. Mypy in general makes certain patterns which are pythonic not typecheck whilst pyright is a lot less painful in that regard.

I've personally found that dealing with mypy has been more noisy and painful than using pyright and leads to a lot of users/other devs just ignoring typing altogether.

I think that type checking has to closely match the semantics of the language and if there's a gap, it will often push users to do the easy thing, which is just ignoring checks.