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?
Yes! I started like a year ago and am very happy. I strongly recommend mox. It’s lightweight and the configuration makes it very clear how to set it up properly. I had some weird issue with sending mail to Apple accounts but (believe it or not) I reached out to Apple and they seemed to fix it.