It's about trade off. A language that keep getting new features every year, will make some users happy, but will lose compiler speed and it will be harder to learn.
I hope for C#'s sake that at some point it can metamorphize--not just evolve--into a new language that can leave some of the crufty decisions behind.
That's being a little too harsh, in my opinion. Even if you were designing both kinds of nullable types right now, it'd be difficult to have them behave the same way without adding runtime support for keeping track of nullability of reference types. And that's quite a big task.
To me, VS 2019 refactoring suggestions and Roslynator extensions helped a lot to learn and use new syntax capabilities and idioms: you write code in "the same old way" and then often roslyn is able to convert this code using new features, often in a concise, readable but undebuggable way :)