Your Python installation seems to be broken and/or you have a mix of packages from multiple sources. The virtualenv command no longer works, Python fails to import ssl which is part of the standard library, etc.
Did you install Python packages to your system outside of Rasbian’s repositories outside of certbot-auto and the commands I gave you?
I think I found the reason. Last days I had more strange errors. I couldn’t do apt-get update and apt-get upgrade without an error.
The SD-Card seams to bee broken. I restored a backup to different cards and there everything works.