Python 3 incorporated types into the language itself, in a similar way (though non-reified) to PHP. This seems much easier to deal with than requiring two files (.rb and .rbs) to describe a single data structure.
TypeScript hasn't ever done anything for me than give me 3rd party dependency integration headaches. I love strongly typed languages and compile time checking, but TypeScript has never seemed worth the trade off due to its broken interoperability with normal JavaScript and the terrible state of crowd sourced typedefs. I'm either fighting some badly defined third party typedef, spending a lot of time creating typedefs myself or dealing with a version issue because the typedef isn't compatible with the version of the library I'm using.
When I use JavaScript I hardly ever run into issues that static typing would have prevented and I have zero TypeScript issues.
Honestly how has it improved the speed at which you get things done? Were you just constantly running into JavaScript bugs due to the lack of typing?
Then at the end of the day, it was still JavaScript (an interesting word for "not ruby"), but with types slapped on top.
I ended up switching to crystal, which is basically ruby + types (infered when possible, but I actually wanted the types) with the performance of golang.