I use GoogleMail behind a custom domain ($50/year) and am quite pleased. I used to be a FastMail customer but a couple minor outages and weirdness around billin

I use GoogleMail behind a custom domain ($50/year) and am quite pleased. I used to be a FastMail customer but a couple minor outages and weirdness around billing made me switch a few years ago. Functional "report spam" is a big win for GoogleMail, and as an apps (or is it "GSuite" now?) customer you don't have to worry about ads/privacy issues. Don't self-host, I self-hosted (Postfix/Dovecot) before using FastMail and it was a huge headache between reasonable spam filtering on the receiving end, and undelivered/spam-marked emails on the send side, although I learned a lot by self-hosting. Also, it was hard to pretend I was serious about privacy/security when I was self-hosting on a box that any Linode admin could shell into as root, especially after Linode's security dramas. This is not to say that self-hosting cannot be cheaper and more secure than alternatives, but if you're not a full-time sysadmin regularly setting up mail hosts, you probably will get something(s) wrong. I never could silence that voice in the back of my head saying "what if some really important email couldn't be delivered to/from me?", which was sometimes right. As others have said, you have to use GPG if you're serious about privacy, regardless of your email provider. Anyway, for me, $50/year is a great deal for reliable email with good spam filtering, and being able to use my personal address/domain for Google Hangouts and Docs is a decent win for collaboration.