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There won’t be such case is my argument. No one patches a system “for fun” and automatically there except they really set it up like that. It would be only one kind of a case in one company.
Furthermore, you cannot compare Linux systems. A modem firmware with busybox is not the same as a Debian PC desktop. It works differently and has only the kernel in common. And in both cases they aren’t patched at the same time. They are not even the same version, hell not even the same platform.
E.a. nothing will ever break like this. If it does, it will be one single case of a single IT department.
I’ve been self-hosting Postfix for several years and it’s not difficult, if you’re absolutely confident what you do. I don’t recommend it if you don’t know basic behaviors and internals of SMTP and relaying. Also you need to know how to secure your server so you don’t get spammed a lot and getting hammered with brute force attacks.
From time to time you need to react to delivery problems. Most interesting one is perhaps Microsoft, which you need to ask to whitelist your server or your email won’t be accepted.