I imagine that's what the supported option is going to be. Given that the OpenSSH documentation explicitly lists Cygwin as the way to run it for windows, simila

I imagine that's what the supported option is going to be. Given that the OpenSSH documentation explicitly lists Cygwin as the way to run it for windows, similar will probably happen for LibreSSL. The OpenBSD team has always had another team handle porting of their libraries, and they do a pretty good job of it.