2 out of 3 of the items you wrote down has to deal with old baggage, so whatever form of language you are dealing with those, you aren't going to have a good time. You can either bite the bullet and write the type definitions yourself, or just disable the type system altogether, which, if you can isolate it to a certain area in the code, you are fine.
If you are writing code that some other person is going to read and/or you are interested in having it behave reliably in the long run, I think a static type system is a must. Coupled with good unit tests, if the type checker does not complain, you can be very confident the code you wrote is working and will work for a vast majority of the cases.
Typescript is especially great because, unlike some other statically typed languages, you can choose not do use it in some cases (e.g., setting up mocks for tests, writing a small script to see how stuff works, etc), which is liberating.
I went from Python to Typescript. Python is still my go-to language for random tasks, though unless I have a good reason to do otherwise, I don't want to deal with a production codebase that does not do static type analysis anymore. I don't know others, but I just get more done in less amount of time in this way.