OP, I don't know if you are reading the comments here but in case you do: Don't get discouraged so quickly. The reason this is happening is as the blurb from the MS postmaster help page: Your IP doesn't have a reputation yet. The reason these rules are in place aren't about email monopoly, it's about spam. If anybody could setup a SMTP server and start firing off large amounts of mail, spam would be even more endemic…
Thanks for the encouragement! I might take another shot at it sometime. I had this server running for about 3 months with just my personal mail, sending probably 1 email per day on average. It's possible slightly higher volume would do a better job of "warming up" the IP. I self-hosted from about 2007-2008 and 2011-2013, and had nowhere near as much trouble with deliverability. It came as a bit of a surprise how much…
But anyway yeah the barrier to entry has risen really much. It's much harder these days than just a couple of years ago, and it probably won't get easier either!