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.
When you hit types like that type aliases come to the rescue; a type alias combined with a good docstring where the alias is used goes a long way
On the far end of this debate you end up with types like _RelationshipJoinConditionArgument which I'd argue is almost more useless than no typing at all. Some people claim it makes their IDE work better, but I don't use an IDE and I don't like the idea of doing extra work to make the tool happy. The opposite should be true.