1. I'm a control freak and a privacy freak. I don't trust any third party with my email. I want to know how things work under the hood. And if I want to make a change, I don't want to have to depend on any third party to do it.
2. It's not hard to do. apt-get install postfix and dovecot, invest a couple of hours munging config files, and you're done.
3. Much easier to transition your data if you do get "enterprisey." All your data is on your server, so you can just tar it up and ship it anywhere.
4. You can configure the server so that insecure connections are not possible, making it that much less likely that someone will leak a password accidentally.
5. Stealth. It's much less likely that someone will try to break into my server than into Google's servers.