I stopped self hosting when my host got blacklisted and I lost about a year of emails with my grandmother… I just thought she was reading them but not having the energy to respond but when I visited at Christmas I saw that all my emails were in her spam box.
The unfortunate thing is that more than any other service, email feels like the one on which I cannot risk to compromise reliability. This sort of story (thank you for sharing) unfortunately fits with my own experience managing my University's undergraduate society's local email server. Non-stop headaches and complete indifference from every group which affects your setup.
I don't even routinely use my undergrad's email forwarding address. It's probably better than it used to be but, at one time, it definitely caused more stuff to drop in the bit bucket than emailing directly. And I assume, at this point, that my Gmail account isn't going to go away.
