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 do it. Postfix+dovecot+spamassassin managed with ISPConfig running on a VPS. Works just fine, but my domains already have a long-ish good reputation so that may play a part on my experience. Biggest headache is to keep things running, which occasionally means jumping trough hoops microsoft(mostly) and others throw at you by flagging your server as spam for no apparent reason.