Easier and more painless to just pay another company to do that and not have to worry about server security, spam, the endless SSH requests for ‘admin’, etc etc

Definitely. I do it for fun though. I’m kind of a masochist 😂

Rolling your own email is a pain. That said, I use a VPS and host my own server with domain name and site for $5/month. Setting it up was a pain, but once you get all the records right so you’re not considered spam, it works really well. That said, I haven’t done anything with webmail; I strictly use IMAP and SMTP.

Damn, don’t go giving them ideas!