[jodyribton]

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 more difficult it is these days.

[MortenK]

If you try again, try to see if you can get a client with a decent sized mailing list. Warming up is usually done with progressively larger sendouts. So you'd start with maybe 500 sendouts, then a thousand, then 3000 etc.

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!