I have worked with 10+ different languages, multiple different IDE's, some types and some dynamic, some like shell which doesn't really have the concept of types at all.

If you are encouraging me to try typescript because you think its great, then I would encourage you in return to test python in combination with system and integration tests. It makes for a very safe environment where you know your code is working.

I don't want to speculate why you feel so attached to static languages. I worked with python in 15 years, you in 17. I have done low level embedded C code. I done web development, and shell scripts. Tried lisp, and programmed in Ada. If you have also worked with similar amount of languages and reach a different conclusion then either your work is very different from mine, or you as an other person have a different experience than mine.

When it comes to keeping simple thing being simple, static languages has never delivered for me. In embedded system I live with that aspect, but that's the nature of such environments. The primary question when working with dynamic language is: "is there already a library that does what I want, and how do I modify it to work in my use case". Instead of thinking about structure and types, I am thinking about interfaces.

I will conceit one example where a static typed language is much better than a dynamic typed, and it illustrate the environment where such language aspect shine. SQL. SQL with dynamic types would be horrible and any database which treat types some-what dynamic is a horror to work with. SQL does not make simple things simple, and database exceptions are quite harsh in every aspect. There is also few if any interfaces, so its types or nothing.