Basic email security - why is GPG so rare - etc.

On the second thought, server-to-server is not enough. There is also the server to mail client (via IMAP/POP) on the other side. Who knows what kind of security that has, if any at all.

It seems to me like email is just an overall insecure communications method. If so it bothers me how commonly used it is.

Again, I ask for your thoughts about these issues. Correct me if I'm wrong. Are my worries unfounded?

People gave up on privacy long before the whole Snowden escapades.

For the majority of email, who cares if "other people" read it. Since the beginning of email, it was always advised to treat email like a postcard, not a sealed letter.

Real secure communications requires quite a bit of pre-communication prep (hence the lack of widespread adoption). I find it easier to use a word processor, encrypt that file, then just send the file as a regular email attachment (works as well for moving stuff via dropbox, etc). But I only worry about passwords, financial info, and my plot to take over the government (just kidding nsa).

I think every encrypted email scheme that attempted to make it point-n-click easy, has failed to date.

Thunderbird used to have a plug-in to sign/encrypt email, I don't know if that is current or abandoned.

You best bet….shave one of your slaves head, tattoo the message on their scalp, let the hair grow back, then send your slave to the recipient.

Thunderbird still has enigmail which is actively supported (I use it). All my emails are signed by default, sometimes people send me encrypted mail but only once in a blue moon. The biggest thing against gpg is you can't read it in your web mail client (yet).

Some MTAs will note in the Received: header if TLS was used; many do not (Postfix does not by default).

The Postfix docs tell about how to enable logging of TLS negotiation.