I've run my own email for about 4 years now -- I'm fairly tech savvy, but don't know much about email -- so was pleased that my "quick" solution has worked well

I've run my own email for about 4 years now -- I'm fairly tech savvy, but don't know much about email -- so was pleased that my "quick" solution has worked well. I use Apple Server to host the email via SSL on a dedicated server, really easy to configure. The key thing is deliverability - initially I had some problems with my email going into junk folders. To get around this I send all email via a service called PostMarkApp (http://www.postmarkapp.com http://www.postmarkapp.com) which allows you to setup SPF and DKIM records on your domain and therefore ensure emails are authenticated. I get pretty close to 100% deliverability. PostMarkApp also shows you open / browser stats, so it's quite useful when I wonder if someone has read a particular email. Not sure if this would be secure enough, but has worked well for me with almost zero maintenance after setup.