It appears to me the issue is browser warning dialogs that imply it is always very dangerous. There should be either more context explained in those dialogs or a recognition of/mode for sites that are supposed to be self signed.
This becomes a nightmare, when the original admin in the org is gone long times ago.
Then I thought, WTF am I doing?. I realized that I was making computers that would circumvent the world's security apparatus. Of course it won't hurt if I make no errors of practice or judgement but, am I really smart enough to handle highly radioactive material.
I ripped it all out. It makes me shudder thinking about it.