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?
Been self hosting email for a good while now and it’s been largely painless. My emails are not getting marked spam either. Although my only outgoing mails are to FOSS mailing lists and occasionally to individuals, not for anything business related.
I would say that if self hosting email sounds like something you’d be interested in, then it probably is worthwhile for you. I like being able to configure my mail server exactly the way I want it, and I have some server side scripts I wrote for server side mail processing, which is useful as I have several different mail clients so it makes sense to do processing on the server rather than trying to configure it on my many clients. It definitely falls into the “poweruser” category of activities but I’ve had fun and I enjoy my digital sovereignty.