I'm gloating because I made the correct and educated choice which has saved me from a large percentage of such headaches over the last decade or so.
You are imagining headaches and people running around like crazy.
In real life, these type of events are frequent enough that there are well established processes for dealing with them and they are taken comfortably in stride. It's virtually a non event.
If people can't handle these things easily then they are incompentent and just having OpenBSD isn't going to help much.