Rich is certainly a brighter individual than me, but some of his points are either him missing the point or being intentionally misleading.
For example, he discusses how Either types aren't true sum types because Either<A, B> isn't the same type as Either<B, A>. So he disparages people who say that Rust/Scala/Whatever have sum types. He's missing the point because 1) All Either implementations I've seen have the ability to swap the arguments to match another Either with the types backwards, so it's a sum type in practice, and 2) Clojure has none of it, so why criticize the typed languages by saying their type systems aren't perfect when your language's type system isn't helpful at all? Throw the baby out with the bath water?
To your specific point (which is also one of Hickey's), yes, it does kind of stink that loosening a requirement forces consumers to update their code. However, that minor downside does not mean that Optional is "not an improvement". It's still a HUGE improvement over Java's absurd handling of null (IIRC, Clojure is the same as Java there).
Also, maybe changing something to optional isn't really "loosening" the requirements. It's just changing the requirement. If the parameter changed to optional, don't you want to be alerted to that? Why is it optional now? What will it do if I pass None/null? Maybe I actually would prefer that to the way I called the old version.
It just never struck me as offensive to have to change my code when I upgrade a dependency. I have trouble sympathizing with that mindset.
Edit: And what is the Clojure alternative? You can loosen requirements, but really, you never had enforceable requirements anyway. Is it apples to apples to talk about a typed language loosening its contract?