I’m presuming you have this fixed?
I noted that you tried to install homebrew as root. Don’t do it… it causes all sorts of problems down the track. OSX is very picky now about what appears on the system. Anyway, after some hickups I had, I have certbot running fine and created my certs. I did it the NON automatic way, and left them in the /etc directory where they were put.
I then edited my vhosts.conf file and pointed the SSL setup to the certs. That way, when the auto-update plist script runs, if there is an update, it simply updates the certs, it knows where to put them, and it’s all hands free,
I put a copy of the plist file on this board just previously.
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