1. Apple is not usability testing this 3 year old version of a fork of openssl, because they're not supporting it at all.
2. help text not available because its an apple supplied fork. openssl does tell you to use 'help'
3. man pages do exist. Just not installed by apple like author expected
4. and stop forking OpenSSL; BSD project forked it and Apple wants BSD over anything else because they can put the software in their closed platforms. Even if libressl were on the up and up, Apple's still got a version from 2016 installed.
Those are all Apple problems, not openssl problems.