I tried maybe 15 years ago and it went about as well as you’d expect for back then. But I’m starting to get the itch again.
Have any of you tried relatively recently? How impossible is it to get reliable deliverability to gmail and whatnot these days?
I was actually recently discussing self-hosting email on Matrix a while ago, so I’ll just copy-paste below. Long story short, find the right existing email software you want to use, set it up correctly with a healthy IP address and domain (not blacklisted), the right DNS entries, and a PTR record, and it’ll work just fine.