I’ve been self hosting E-mail (send and receive) with SSL and IMAP, for my family and a few hobby clubs on a $5 Linode VPS for at least a decade, probably more. Very few problems over that time period. Basic exim4/dovecot setup. Occasionally some crappy ISP’s spam filter gets too aggressive but I follow their unblocking procedure and am fine from there. I do keep my old empty gmail account around in case that changes but I don’t use it much.
The fear around self hosting seems overblown. LetsEncrypt falls over more often than my E-mail.
The fear around self hosting seems overblown. LetsEncrypt falls over more often than my E-mail.