[ThePhysicist]

I also write Python with type annotations and the type checker keeps getting better and better, though I find it's often not strictly necessary, at least for small projects. The most important thing is to keep the code simple to understand and follow, then you can write great software in dynamically typed languages as well.

Also have Typescript experience but in general I'm not a big fan of gradually typed programming languages, static typing works best in languages that were designed for it from the ground up and that offer an expressive type system, e.g. C++ or Rust.