I've been self-hosting my email for over 7 years now. Just threw postfix and a couple standard milters on the smallest digital ocean droplet (so it would have a

I've been self-hosting my email for over 7 years now. Just threw postfix and a couple standard milters on the smallest digital ocean droplet (so it would have an IP with a good reputation) and let it go. Had some deliverability issues to microsoft mail services at first but went through a support process that took care of that. Never had any other issues. If you aren't familiar with postfix it can be a pain to setup correctly, but I think there are a bunch of mail server software bundles these days that make the process a lot easier. Pros: I make pretty extensive use of aliases (every service I give an email address to gets a different one) so it's nice having such fine control over where emails are routed, but mostly I just like not needing to rely on a mail provider. Cons: Small ongoing cost and initial setup efforts, but no extra effort once it's setup - I haven't had to do any management work on the server in years.