In my experience, the right tooling makes Python typing a big win. Modern IDEs give comprehensive real-time feedback on type errors, which is a big productivity boost and helps catch subtle bugs early (still nowhere near Rust, but valuable nonetheless). Push it too far though, and you end up with monsters like Callable[[Callable[P, Awaitable[T]]], TaskFunction[P, T]]. The art is knowing when to sprinkle types just enough to add clarity without clutter.