I host my own email. I have been running email servers since the 1990s so it is not hard for me. I run postfix with SpamAssassin on a Debian VPS, and usually

I host my own email. I have been running email servers since the 1990s so it is not hard for me. I run postfix with SpamAssassin on a Debian VPS, and usually use alpine to read it. I have SPF records in my DNS and such. I have not had trouble sending to Gmail. On important emails to Gmail addresses I BCC my own Gmail account. If my account does not get the mail I figure there is a problem. For me it always goes through. My setup is stable. In the past ten years I had my current setup, but also other domains hosted via Google Mail, or by my hosting providers etc. They all had migrations, discontinuations etc. I migrate them all to my mail setup. I have no such hassles with the email servers I myself set up. It does not have large changes (by servers I mean the primary and queuing mail servers). I have a lot of experience doing this though, not sure how hard it is for others, but it is a lot easier than the old days of configuring Sendmail with m4.