As somebody who's comfortable with Python and C++... ugh. Types are frankly kinda silly. They don't
do anything, the language doesn't even ship a blessed typechecker, they don't speed up your code, they don't make it safe, they just add useless notation that some mutually-incompatible third-party tools grok. And the mutually-incompatible thing is what really rubs me wrong. They didn't sit down and define a bombproof type system; they just added an optional notation and let the community figure it out (like packaging). Years later, and the community has not figured it out (like packaging).
Compared to C++, where you can do incredible zero-overhead magic with the type system; for example duck-typing, once The Way, is now an absolute nightmare in Python's type system. Python typing is little but baggage and warts unless you've drunk the cool-aid and then you're horrified that people like me haven't.
(and, all that said, I'm quite excited about py3.11, it's great on performance and ergonomics)