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One of the biggest hurdles I've experienced is that a number of large players in the industry (think G..argantuan) systematically flag private mail servers as spam almost as a matter of course and it's up to you to prove your innocence. There is a clear financial benefit for this sort of behavior as it pushes people back onto their services.

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The bulk of this post discusses IP reputation which is the biggest hurdle to self hosting. It is the first line defence for spam/phishing/fraudulent mail. SPF and DKIM can align for DMARC, but if the IP has a bad, or no reputation, chances are the message will be bounced. Think of it like having a low or no credit score. As an example, if a “cold” IP address suddenly starts sending mail, mail security will take the (arguably cynical) view that chances are it’s some sort of spam. It even more cynical to assume that this is done as a money grab, shepherding users to big mail services, when in fact, it’s the best way to prevent bulk mail.

The irony too is that, if you run a mailserver of substantial size, you will become very sympathetic to the other side on this. Dropping email from new/suspect IPs will tremendously reduce your user complaints about spam. It's not really a winnable situation.

Monopolies gotta monopoly. In the end though they can't lose too much of their incoming email before people will move to email services that are reliable.

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