Sorry for the revive of this. However, this would be amazing if it could be implemented/coded. Imagine having a town with 500 people. I'm going to spend a whole day trying to send those people mail. Even 30 people. The normal-ish town size. That's about 2 hours of my day still. (I have to up arrow, delete the name, rewrite the name, and maybe the name is too long for the message, so I have to send them two.)
While it is only a convenience thing, it would set Meep apart from other basic towny plugins/servers.
+1