The problem I outline is not that static typing involves additional boilerplate. It's the inherent additional cognitive load it introduces. A smarter compiler isn't going to help you there.
The fallacy of Elben's argument is in the assumption that there will be only advances in the field of static typing.
Meanwhile, people working with dynamic languages are improving their tools at an astonishing pace. For example, working with an editor like Cursive provides many refactoring options you could only expect from a static language a few years ago.
The biggest benefit though comes from interactivity though. Dynamic languages lend themselves extremely well to providing live coding environments. This allows for tools like the REPL and things like Figwheel https://github.com/bhauman/lein-figwheel and this kind workflow will be difficult to match for static languages.