I took the liberty of turning your images into attachments. I couldn't read it as it was, and the post also violated forum rules.
Have you tried
https://dave.com:44344/?
I use SSL with CC. My content server is set up behind apache. Apache handles authorization (user/password) and forwards requests to calibre using the
rewrite rules described in calibre's manual. Since my apache server listens on the standard port 443 the url
https://my.server.org/library works. However, I just tried
https://my.server.org:443/library, which works as well. The URL
https://my.server.org:444/library does not work, which demonstrates that the port in the URL is being respected.
This web page seems to describe what you want to do, use stunnel as an https proxy to connect to an http-only web server.
NB: CC doesn't do certificate management, so self-signed certs won't work. CC must be able to validate the cert with some known authority.