[ValdikSS]

I'm running 4 email servers, the oldest is from 2011 or so, to this day.

4 different countries, different AS.

I'm always puzzled by all the issues described by others. I had about 4 issues during these 15 years, all 4 were solved by reading the bounce message and doing what was asked in the message (contacting support of the destination).

[nijave]

I had a Digital Ocean VPS and it was fine about 7 years but on year 8 the entire /24 got blacklisted and it was game over

Took about 6 months initially of fiddling to get other email services to accept mail DKIM, DMARC, SPF, PTR, web form requests

[dizhn]

I had the same experience. Since 2008 or so on Hetzner of all places too. Their IP reputation is supposed to be shit if you believe any HN post about self hosting. I had issues maybe 3 times. The most recent of which was 2 weeks ago. I read the message, sent the postmaster of a German telecom my two IPs and they added them to their whitelist. That was it. Also postfix+dovecot+rspamd is enough. I have rspamd on the gateway that passes on clean mail to my real mail server.

The comments (not parents') are usually very weird like people are mad at us for hosting our own mail server or something. That is really an interesting phenomenon.

[Krei-se]

Same. People just remember it's hard because they don't test, don't like responsibility much and esp. because they test this in production not on a spare domain. Then all you remember from it is the 10 people shouting at you and that you need to fix it NOW and it's all super stressful so they never attempt this again.

[chappie7]

A lot of the people who complain that their emails were treated as spam when they tried self-hosting leave out that they were really sending unsolicited commercial mail.

For personal email, self-hosting is much more manageable. Typically GMail will send those messages to spam at first, but after a few different mailboxes have clicked “not spam” GMail learns the lesson.