[ufo]

Indeed, gradual typing and optional typing are more along the line of adding types to a dynamic language. The kind of dynamic typing you were talking about looks more similar to the Haskell's Data.Dynamic type or the "dynamic" type in C#. It works great to add some dynamicity to the language (for example, to interoperate with a dynamic API, or to code metaprogrammey stuff like reflection and serialization) but you can't use this to bridge the full continuum between static typing and dynamic typing, which is the design space that languages like Dart and Typescript are trying to tackle.

> It depends what you mean by an accurate type.

The gradual typing literature tends to prefer having partial functions (that might raise well-behaved type errors at runtime) because it eases the transition between typed and untyped programs. You can add or remove type annotations without having to simultaneously add and remove tons of explicit pattern matches against Maybe. But this isn't the part I was talking about.

The key issue is that when you cast a function from (Variant->Variant) to (Int->Maybe Int) you need to add a small wrapper around the dynamic function that converts the input from Int to Variant and converts the output from Variant to Maybe Int. In theory it is simple but in practice all those wrappers can add up really quickly...

Functions are the simplest case where these higher-order type-conversion issues pop up but in my experience things are actually the most thorny when it comes to mutable objects and arrays. The extra type checks and conversions around every property read and write can add a ton of overhead. And from a semantics point of view you need to be careful because if your implementation is based around wrappers it could end up messing with object identity (like Javascript's === operator or Python's "is")