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.