The biggest problem Swift has is breaking changes from a version to another. Took me about 10 days to manually convert a Swift 2.5 project to Swift 3 to find out that Swift 4 will also introduce at least two breaking changes. I'm all for progress and modern ideas in a programming language, just don't break my old code!
I doubt that they want to, but it is really hard to redesign something you didn't get right the first time in a programming language, without breaking some code. The choice is then to leave the bad design as is, but be stuck with it for the next few decades, (which would be kind of terrible, given Swift was meant to eventually replace ObjC precisely because of this), or you can suffer the pain now, while relatively early, to not have to suffer latter.
I think they made the right choice, in terms of prioritising long-term benefit over short-term gain. ObjC is still fully supported for those who want it and in the meantime, we can get a more perfect Swift.