In particular, dealing with Core Data can be a holy mess with Swift because every single property on a Core Data object is dynamic and implicit optionals. Unlike Objective-C, which will happily pretend like nothing has happened (in many cases), Swift will explode quite spectacularly if you try to operate on nil values, and implicit optionals lets that happen without throwing type errors. Either be very careful with marshalling accesses to Core Data objects, or test thoroughly with different data patterns. Last thing you want is your app crashing because someone filled in data in your app that leaves a property set to nil.
I'd expect some resistance (on top of the "I need to learn a new language" part), and some swearing about all these "if let"'s or "I thought Swift meant no more null pointer exceptions!", but it's perfectly doable.