- Optional is a nuisance and I don't think it is highly effective at preventing the dereference of a nil pointer in practice. People are going to fiddle with ? and ! until their code works, and the protection that Optional provides then disappears.
- "let" is a mess. In one context it means unwrapping an Optional. In another, it doesn't. If you use it in an expression, it interferes with the usual refactorings that people apply to expressions.
- There is so much fussy detail around preserving the syntax of object.field = expression. didSet, willSet, getters, setters, oldValue, newValue. WHY IS THIS SYNTAX SO FRIGGIN' IMPORTANT? One of the justified criticisms of C++ (IMHO) is that operator overloading means that all sorts of functions can be running under innocent-looking code. I would much rather have = mean assignment, and use function call notation when I really want functions to run.
- Reference counting is a bad compromise between the unpredictability of GC, and the burden of explicit memory management. It's mostly unobtrusive, but I've seen examples of code that require careful and non-obvious use of weak to avoid memory leaks, (sorry, I don't have the reference handy).
It sure beats Objective-C, and it does have some nice modern features, but I think they made some unfortunate design choices.