To what extent do you see Python drifting toward stronger typing? I ask because after 10 years without touching a single line of Python, I recently worked on a Python code base and I was very positively surprised by the static typing that's available in the language now. Not even necessary to to reach for additional tooling like JS and TS.
Drifting? I think it's there. basedpyright is awesome and super fast. Our latest services are all CI gated by type checking. Early in my career you'd hit so many dumb errors running your code - NoneType, attribute, value, and type errors. I'd say that's been cut over 95%.
What tooling are you thinking of that’s part of the language? I don’t think CPython ships with a type checker, does it? People typically use mypy or pyright and neither or these are part of the language.
Python is a general development language that can be used to build servers and web pages, but does a lot more besides.
They're not really comparable.
Having said that - I wouldn't be surprised if Python drifts towards stronger typing, although it will probably remain optional.