Earlier quoted context omitted.
That's not universally true - there's a remarkable amount of TLS/SSL encrypted email-in-transit, either via STARTTLS ESMTP commands or SSL over port 465 (and 993/995 for IPAM and POP3). I don't think there's a way to guarantee your mail always travels over TLS/SSL secured connections, but I suspect more of it does than you think.
There's a straightforward way to make sure your email is always encrypted in transit: encrypt it before you send. No promises about making sure your email can always be read by the recipient, though...
This is a hard one to solve. GPGmail seems to get broken with every Mac Mail.app release. Vast numbers of people rely on webmail - which'd need server-side or in-browser GPG decryption. My Mom's not going to use command like gpg tools. How the hell do we bootstrap our way up to ubiquitous encrypted email?