I run my own obscure mail server and have not had an issue in years, except for ATT[1]. I'm super low volume - I run mail for about 20 humans, a few mailing lists, and some other automation that does things with email.
I do things correctly - I mean, I run nearly the same stack/configuration (scaled way down) as I do professionally for my employer, which delivers 8 digits of messages a day all over.
But that doesn't explain why I don't have problems and others do - lots of people get this right and still have problems. And I think that comes down to the fact that mine has been on the net since the mid-90s. So, unfortunately, I suspect the answer to a lot of these problems is 'exist for long time' - until your MX is associated with a bias towards "not spam" in everyone's filters.
I can think of ways for existing mail servers to vouch for new ones, but I don't think there's any reason for established ones to want to do that, so it wouldn't work. I'm not sure what the answer is.
[1] And after many, many years of attempting to resolve it, they can bite me. I got annoyed enough that they get a custom bounce from me now on the rare occasions someone tries to spam me through them.