(Maybe Dr. Phil Wadler's work would help advance things beyond the suck, but...)

So far from what I have experienced with Flow, Typescript, and Typed Lua, and from what I have read about wrt e.g. Typed Racket, I have to say that if your core programming language doesn't come with static type checking in the first place then it is a fool's errand to try to save the dynamically typing people from themselves, or me from them, or them from me, or anything from anybody.

The core problem is interop. You are very likely going to need to use other libraries, and those will ruin your attempts at having a nicely type checked life.

Similar argument goes for things like Shen, I think: there's not enough libraries, and you there won't be a nice way to automagically wrap up existing libraries with types that work. Look at the failure of Definitely Typed, or flow-typed, etc.