TypeScript has a comparatively easier job because the type system is unsound. They can add new type features without needing to be paranoid about a hole in the system or a usability pitfall because the tools don't rely on types for correctness or optimization, and because users can easily cast to "any" or otherwise work around an annoyance.

When you want the whole system to actually deeply rely on the static type system, it needs to be much more robust, and that takes a lot of effort.

I'm not trying to minimize what the TypeScript folks are doing — it's a really nice, well-designed language. But the complexity required to evolve an optionally-typed language is closer to that of a dynamically-typed one than a statically-typed one.