So, after some reading on the jboss-cli I think I spotted the issue, but not confident enough to question the source in git yet. In looking at the "configure-https.cli" file I noticed the 2 main command lines have a double forward slash "//"... which didn't seem to make sense with some of the command format examples I had seen. After removing one of the forward slashes on each line the command will complete.
ALSO seems I was calling the windows jboss-cli.bat command from cygwin shell... which was acting flakey for me in interactive mode. When I started the shell from a built-in Window CMD window I could make things work (testing commands, calling "help", etc.).
Am I missing something with the prefix slashes?