Thank you...

From what I've read so far on SSH tunneling with server, is that you'll
need to have the same setup on both sender & recipient machines, in order to
do the encrypt/decprypt task.

Not that I mind my ISP from knowing that I have a server, but I think TOR
suits better.

I've used TOR+Privoxy to surf the net before, just not sure on how
to encrpyt email contents information with it.