I've always found this to be a silly argument. In both cases, the problem can be solved by interface versioning. If you have f : T → Maybe T and you should like to change the type, just create f_v2 : Maybe T → T assign f x = just (f_v2 (just x)). The real shame is that most languages do not support interface versioning as a proper feature. There should really be some way to use a package and declare that you want to use v1/2 of the interface, then subsequently package.f would either be f or f_v2. You would eventually have to change the code that deals with f if you want to stay up to date, but realistically you should remove redundant error checking code anyway so you aren't much better off.

You could also frame it as a tooling problem. Given that the transformation between types is trivial, you should be able to write a program that automatically updates code to newer versions. It seems like this is a relatively niche issue in either direction (union types not being disjoint, vs having to change code that deals with options), but its a more solvable problem in the second case.