Does anyone self host email anymore successfully? I'm honestly asking. I would like to but it seems like a full time job trying to keep it running. Are there halfway solutions where maybe you own the service and domain and it runs somewhere trusted?
I have switched servers regularly, mostly between OVH/online.net/Hetzner since they are the three big cheap European hosts. I have also used various server software, now happily running OpenSMTPd.
I have had a few problems with Microsoft in the past but contacting them (what made me care enough was marrying someone with an @hotmail email address) eventually fixed delivery for good. No notable delivery problems otherwise. I also run my company's mail server, it works fine too (with a much larger volume and different usage patterns), also running out of OVH servers.
What I recommend for people who don't want to do sysadmin is buying a domain at OVH to use the free email service offered with it. It's cheap and works, and it's easy to switch to another registrar or provider if needed.
My IP has not changed since 2010 and I have perfect dkim/dmarc/rdns and whatever duct taped bullshit de jure is currently being practiced.
Everything generally works.
My setup: I have a root server with DNS attached to it. On there is a postfix, with a minimal config that forwards all emails to my real address on posteo.eu. And posteo has not given me any trouble with any of my emails at all.
I use this setup, so I can easily give new email-addresses to individual web services, and it gives me the option to selectively block these addresses.
Last year I brought the big abo from proton, which includes throwaway mailadresses, and I am thinking about migrating my mail setup there.
Not sure though what the magic ingredient is. I've had the IP address for 7 years before I decided to use it for mail, after one quick mail to Cisco's Talos stuff everything was fine. Software is Mailcow. Hosted at Hetzner in Germany.
And still, I cannot deliver to T-Online, so there's that.
The basic setup has more or less stayed the same, but there's some more extra components around it you have to know now (spam filtering and SPF/DKIM/DMARC come readily to mind).
To quote Michael Lucas: "everything complicated about emails revolves around spam and not getting it". I highly recommend his book, "Run Your Own Mail Server".[1]
In short, hosting your own email is not that bad at all. I strongly suspect, like many other skills, since it has atrophied with the advent of the cloud and people readily giving up to the large carriers, it has gotten the reputation of being hard, or as you said, a full time job. I don't think either of those things are true.