I've found that it's pretty easy to slowly enable mypy checking. You can mark modules with "type:ignore" to make mypy ignore them. Then, you can move to marking individual statements with "type:ignore". Finally, you can start marking modules with "mypy: disallow-any-generics" at the top. That requires that functions are annotated with types.

In a large code base, our team has found type annotations and mypy to be quite helpful. If you are writing a quick-and-dirty script, forget about wasting time with type annotations. However, for long-lived and important code, it seems to be worth adding the types.

Another thing I noticed, if your type annotations are hard to write, e.g. lots "Union", "Optional" or deeply nested type expressions, it's probably a sign that your code is poorly designed. Think about what types you actually want to consume and return. Define new containers using dataclasses or attrs to keep the types simple, if required.