2. The issue the author complained about was `openssl --help` not working, and it doesn't work on any platform (because he got the command wrong). `openssl help` does work on OSX (I literally just tested it).
3. Yeah, that's the one issue we agree is an Apple issue.
4. Apple didn't make LibreSSL. Other systems besides Apple use LibreSSL, and the authors complaints about their lack of documentation are relevant regardless of what Apple does.