> Sort of like a monad, even!
Yes that's it - they're monads! Either is also a monad, and you can store error information in the other side if you want, but a good thing about Maybe is it could transparently store the error information, and produce it when debugging, rather than baking it into the normal runtime semantics.
> you basically have to trust that callers respect your contract with these types
This is table-stakes for a dynamic language like Ruby, though. Yes people can do anything, but usually they follow the rules they're given.