How to handle encrypted and unencrypted http connections through a single port

Solution 1:

One port to rule them all, shows someone has atleast implemented it in the java world.

Have you ever deployed such a solution in a production environment?

I have not -- nor would I ever recommend it be done. As a consultant I try to encourage my clients to use standardized and proven technologies. No system seems to properly implement those RFC's except for edge cases -- and that would not be something I would want to suggest or support.