The basic foundations of a Windows port are already in place for Crystal, merged into master. In fact you can can already cross-compile a "Hello World" on Windows.
This means the port is in a place where the community can pitch in and help port little bits of the standard library, and help bring it into a release-ready condition.
I'm sure the crystal devs have done a great job, but again let me echo, just because I can write code at an intermediate level, doesn't mean I'd have a clue where to start or what to do in a project like this. I suppose you can never learn if you don't jump in, but it would be very difficult and time consuming. Maybe if there was a way to specify exactly what needs to be done so those less saavy could be directly pointed towards where to help? I'm not sure how this is really done.
This means the port is in a place where the community can pitch in and help port little bits of the standard library, and help bring it into a release-ready condition.