As far as Webmail goes... I agree that your own
server for sending e-mail is great, but unless you
have the ability to send mail direct via port 25
you will be just spining wheels... or if you own
your own mail server(s) like me and your ISP
is a nice guy....
Just remember e-mail is not sent encripted
under normal means... The next best
way I see if there is a server to server and
user to server encription that is invisible
to the normal user.....