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?
Indeed. Owning your mail is a spectrum. I think it’s really best to transition from something like gmail to fully owning the stack in steps, over a significant amount of time. It will take a while to change over the address on everything a while anyway. No real need to go whole-hog right away and then burn out.