- Setup was largely painless. Main problem was making sure dns settings at my domain registrar were correct.
- Almost zero problems with mail delivery on the big providers [1]. Last time my email was dropped was by amd.com.
- Last year had to do a major version upgrade to mailinabox and it was a huge hassle. I think they need to improve on this. Rolling updates are painless.
Here is my advice to people who are on the threshold of wanting to host their own email, but are unsure because of mail delivery issues. Well, there are zero problems with incoming mail. So setup mailinabox and use that email to register for websites [2]. Use it for all your mailing lists etc.
Do it for a few years and see how it feels. Occasionally send out email. If enough people do it, then over time it will become easier for more people to host their own email.
[1] I have a theory that I deployed. I asked a whole bunch of people with gmail/hotmail email addresses to send me emails first on my new email. I then replied to them. I think this ensured that from that start I was put on the good lists.
[2] Use websitename@yourdomain.come to register. Easy to block spam this way.