I've only used Mypy so maybe I should try some more typecheckers. But I've found Mypy and the annotations it uses don't get in the way much, and they make function signatures usable as documentation, so they're generally a win. But they do let a lot of incorrect code through that would have been caught by typechecking in e.g. Haskell. Thus the idea of using 5 typecheckers (not serious I hope, but I understand the sentiment).
I hate JS and have wanted to try Typescript. Is it really JS with type hints? I had thought it was really a different language that compiles to JS, like a less hardcore answer to Purescript. I did like what I saw of Purescript but it never caught on.
I feel like Python itself lost its way during the Python 3 transition and now seems declining like Ruby. IDK what to use instead for low-boilerplate projects though. So I still use Python.