Last time I checked, only State Security self-hosted.
I was probably lucky, but I rarely had delivery problems. The last one was a couple years ago with Microsoft swallowing my emails and it was due to the combination of a fairly old exim and a TLS certificate verification quirk at *.protection.outlook.com. I found a fix in the form of a configuration option somewhere on SO.
In all fairness, there is very little maintenance involved, and whenever I have to do maintenance work, I take the opportunity to learn something new. Like this year, I decided to finally replace my aging Debian jessie setup by Arch Linux, and I rewrote all cron jobs as systemd timers.
I must admit that when I send a really important email, I check the mail server log if it went off without errors, but this does not bother me as checking logs manually once in a while is a good thing anyway.
Lastly, a piece of advice: treat self-hosting like a hobby and learn to enjoy it.
Oh and the very last thing: the person who designed Exim configuration for Debian deserves a special place in hell for all the hours wasted. If you set up Exim on Debian, just figure out how to use the upstream exim config and adapt it to your needs.
Can or wish to?
Edit:
"After self-hosting my email for twenty-three years I have thrown in the towel"
https://news.ycombinator.com/item?id=32715437
https://cfenollosa.com/blog/after-self-hosting-my-email-for-...
To get whitelisted you have to apply with them and your domain HAS to have a website with an Impressum, your clear legal name AND an email that is NOT your domain for emergency contact. It is insane. If every provider would act like that, email would die in a month.
> The elephant in the room is real-world deliverability. With self-hosting you risk not receiving mail or someone missing your mail. I accept this for my personal projects, but you may not. Keep this in mind.
Pre Gmail I was on Exim. Now I'm on Postfix. I used the 123qwe.com tutorial as a starting point.
The real problems are (1) family members just want Gmail and (2) I have to maintain an email system.
I really don’t want to live in a world where only two or three companies run email for the entire world, and this is my little act of resistance.
Anyway, I added a disclaimer at the top, so people don't treat this as a production ready setup.