I'm definitely a fan of Crystal of though as a project and would really like to see a bigger community and more libraries etc.
The real reason they don't do it is because they can't. It's inherently unsafe. In order to always be sure something is never null you have to be aware of what all it's inputs are so you can reason about it. That's not possible with runtime metaprogramming techniques.
I dunno I guess I just think it's an odd choice. Don't get me wrong, it's a neat experiment and I value it. I'm just slightly miffed that that particular experiment had to mixed in with what amounts to a statically typed language with the beauty and simplicity of Ruby but the friendliness and discoverability of static typing.
Better Windows support could make wonders.
The problem with Crystal is more with the small community than the concept itself which is pretty good IMO.