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I watched a talk, "fun with email" by Dylan Beattie, and his personal advice was "dont bother self hosting unless you're using it for contacting other self hosted users".
Without the dedicated IT support and clout of a large company he said you're gonna spend more time asking other servers to whitelist you than you're gonna actually spend using your email.
Is that something you can corroborate?
That's not true. I run my own email server for 15+ years now. There are only 5 of 6 mailboxes. I never had a problem with any other host. Not Microsoft, not Google. Maybe, the reason was, the IP was also 15+ years assigned to the same domain. I have only known senders, family and friends.
The last days, the hole subnet was blacklisted on some blacklists. So that was not my fault, the growing business of the provider lead to this situation. Eventually I moved to a very small provider and run a mail cow on a vps. On a fresh IP without any reputation. Same 'customers', the only issue was with T-Online in Germany, but a mail solved this. To keep this kind of issues away, I use sendgrid as a SMTP forward. With only a few mails per day, this is free. Mailcow provides a lot of features, rspam filtering, a lot better and faster than spamassin. Active sync, imap, webmail, everything. Solid backup, runs without any problem.
Fun with email was a great talk.