It's worth using a type checker for long enough to get a feel for how it can find bugs that would take you much longer to find at runtime. From there it's pretty easy to imagine how languages designed from the get-go to do this might do it even better.

It's also worth asking if the people who read your code are going to disengage when they see a big pile of type hints. It can be "better" in some abstract sense and still worse for the task at hand.