Update: As of macOS 10.14 Mojave, macOS Server has been gutted and no longer include websites. This guide only applies to versions of macOS Server prior to macOS 10.14 Mojave.
Apple’s Server app can make basic sysadmin functions really simple for a novice webmaster. It can also make managing multiple websites, specifically multiple SSL websites, a nightmare.
I’m a firm believer that everyone should be using HTTPS for all their websites even if they do not use eCommerce. You don’t see me selling anything on this website (at least, not at the time of this post), but yet you’ll find that your browser is displaying a lock next to “itim.co” up above. It’s just the smart, safe thing to do, and thanks to the folks at Let’s Encrypt, you can have all the safety and security that comes with HTTPS for $0.00.
This isn’t the place to debate the merits of using macOS Server over virtually any Linux distro or Windows Server. This is for the green sysadmin-in-training with a Mac and nothing else who just wants a secure website (or four).