Have you worked with TypeScript? I’m working with both every day and I’m always frustrated by the limits of the 'type' system in Python- sure it’s better than nothing but it’s so basic compared to what you can do in TypeScript. It’s very easy to use advanced generics in TypeScript but a hell to do (sometimes outright impossible) in Python.
Yep, although never in a project of a similar size. One advantage of the Python setup is that the types are ignored at runtime, so there's no overhead at startup/compilation time. Although it's also a disadvantage in terms of what you can do in the system, of course.