Swift is another one that has had a really bad migration between major versions, I can’t really remember now but it was either 2->3 or 3->4. They had a static migrator and it barely helped, it would get into loops where it would e.g. flip flop between two different uncompileable fixups.

Seems like this is a really hard problem, what is an example of a platform that has solved it perfectly or is even close? Swift was a brand new language, it should be easiest to do it there vs any system with legacy (although it was designed to interoperate with ObjC, so… maybe legacy remains).