I don't care to unpack most of that. But what I will say is that I recommend automatically backup up jenkins nightly, I accomplished this simply by commiting jenkins_home to a git repo and pushing every night.
These days you can also use the Configuration as Code plugin and you can automate the setup, version control it, document it, etc: https://www.jenkins.io/projects/jcasc/
Jenkins tends to suffer from extremely poor state management and experimenting with things can cause a permanent loss of value to companies if backups are not properly configured - compared with a system like ansible where recipes will grow and be regularly committed to a repository Jenkins doesn't have a nature version control system and as a result strikes me as extremely brittle.
I almost wish the UI for jenkins simply didn't exist and it actually was just a whole mess of config files and shell scripts so that it could be locked down to a much better degree.