To give a concrete example, suppose that you have a weighted graph whose weights are integers. Code to find a Minimum Spanning Tree will always have an integer for the weight. Great. But if you add that type annotation, you'll run into trouble when someone checks whether the previously found MST is unique by calling the same algorithm again using as weights (weight, edges_in_common_with_prev_mst). (This will find the MST that shares as few edges as possible with the original, so if there are > 1 you'll find a different one.) Those ordered pairs were just fine in the original code, but don't fit the type annotation.

Of course, you want to use data correctly. There was a study of server code in Python that found that lots of playing fast and loose with type information happens just after startup, but then types settle down. If the initialization can be isolated in certain parts of the code base, it would make such date easier to use.