Has anyone had good luck with auto-annotation of types of existing codebases? Either via LLM or via various runtime hooks? I work in a codebase that started off in Python 2 and isn't annotated with types in the majority of places, and I feel the pain every time I have to wonder what exactly the arguments to a method is.
Yep, I've used this pretty successfully, the ideal is to run it under realistic prod traffic over time to capture as many types as can flow into a given function, but a good set of unit/integration tests can also provide good coverage.
And if you re-use the same type store (SQLite DB) across multiple instrumented runs, you can further improve it.
https://github.com/Instagram/MonkeyType
RightTyper is much better in addition to running orders of magnitude faster.
https://github.com/RightTyper/RightTyper
(full disclosure, I am one of its authors).