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?
If I had to make one suggestion, I would use a trusted third party to relay outbound e-mail such as AWS SES, mxroute, sendgrid, mailgun, etc. When I was looking for a job a few years ago, I found many potential employers’ systems would flag my e-mails as junk or simply delete them, and I had to revert to gmail. My second suggestion is to properly set up TLS/SSL for security, and SPF, DKIM, and DMARC for maximum deliverability. I’m currently using a deprecated application, but I’ve been testing mailcow which seems alright.
Beware that Mailgun doesn’t differentiate between transactional and marketing emails, this could hurt your deliverability.