If my connection to my SMTP server is encrypted and my receiver's POP connection is encrypted, is there really a need to encrypt the message itself?
The benefits of encrypting the message as well as the transport are mostly for dealing with that fact.
PGP gives you end-to-end encryption, which starts from your computer and ends at the computer of the recipient.
It will be a wonderful day when the RFCs are updated to require TLS for SMTP.
http://www.postfix.org/TLS_README.html#client_tls_encrypt
Depending on your environment you could also do the same thing and require DANE:
http://www.postfix.org/TLS_README.html#client_tls_dane
I am sure exim has an equivalent setting (maybe not for DANE).