I'm on 12 years of self hosting email and counting. Once every so often, I do end up being blocked, usually by Outlook and once by Yahoo. I'm in their 'sender program' and they still don't actually bother to contact postmaster@, but a few emails is usually enough to unblock the block within 24h.
Agree with a sibling comment that many major providers fail to operate the SPF/DKIM/DMARC tools they insist you do.
Each to their own, but ultimately if we don't hold on to the freedom to operate our own mailservers, it will be taken away through inaction. This means doing some things right: DMARC, DKIM, SPF of course, server maintenance, good password policies and of course IP reputation. The best way I can recommend for IP reputation is to use a dedicated provider or VPS provider that disallows things like VPN endpoints, where it is less likely they'll assign an address with a poor reputation. A good provider might also ask you what you intend to host, and you might be able to discuss IP addresses with them.
Agree with a sibling comment that many major providers fail to operate the SPF/DKIM/DMARC tools they insist you do.
Each to their own, but ultimately if we don't hold on to the freedom to operate our own mailservers, it will be taken away through inaction. This means doing some things right: DMARC, DKIM, SPF of course, server maintenance, good password policies and of course IP reputation. The best way I can recommend for IP reputation is to use a dedicated provider or VPS provider that disallows things like VPN endpoints, where it is less likely they'll assign an address with a poor reputation. A good provider might also ask you what you intend to host, and you might be able to discuss IP addresses with them.