Erik,
As usual, a timely post. While encryption itself is not overly difficult, management of the key pairs is a royal pain. I try to keep it simple for our clients and tell them not to worry about encrypted e-mail unless it is required by clients as you mentioned. If they need to send information via some electronic communication scheme, I tell them to put the data in a password protected Word or PDF document as an attachment. Having an open password on a Word or PDF file encrypts the contents. The caveat is not to use a dictionary word as a password or to state the password in the message contents. Duh. :-)
-john-
