The optional typing in Python is pretty mediocre, especially in comparison to something like Typescript that just does everything so much better. The types are pretty limited and not very ergonomic (especially when using generics or functions), and third party support is hit-and-miss. The worst thing, I think, is that the Python typing community are trying to solve lots of the problems with plugins rather than by improving the capabilities of the type system. This might produce better results in the short run, but in the long run it makes things more complicated, as for a given project I need to understand (a) how Python works, (b) how Python types work, and now (c) how each of the plugins installed in this project work and how they interact.

I really want to like typed Python, but it's a pale shadow of what it could be, and what it really needs to be if people want to use it to describe very dynamic Python programs.