But in a non-technical organisation, who should those messages go to?
Often the initial LetsEncrypt setup will be handled, correctly, by some IT staff. Then it might break several months or years later for some odd reason.
The organisational challenge is to get the message through to someone who understands it and will act on it.
This time the problem was LE all of a sudden decided to start storing my certificate in a directory called mydomain.com-0001 instead of mydomain.com, breaking the rest of the setup that relies on things being in the right directory. Automation is only useful when the software behaves predictably and consistently.
So if renewal fails you should have ~30 days to fix it.
But this does work best if your tools try the 2-month renewal. (I'm looking at you, wpengine!)
Yes, and to keep a very infrequently used channel working and up-to-date.
Hence efforts like https://tools.ietf.org/html/rfc8701 - designed to make sure extensibility options don't get messed up.