Maybe the makers of Crystal need to take a leaf out of Go's book. Despite the Go creators not being windows users (AFAIK), they support Windows as a primary target, to help adoption, I assume.
Of course the Crystal people probably don't have the same number of developers working on it as Go did even early on.
Edit: Go took a little while to support windows, not until around July 2010. See this question from November 2009: http://stackoverflow.com/questions/1717652/can-go-compiler-b...