I2P's Bote is better than PGP because it encrypts the headers too, except for the destination address. But all your recipients need to be using I2P-Bote too.

Realize that any email encryption won't hide whom is writing to whom. It only hides with encryption the content in the email. But this is no good! If the officials can prove whom you were communicating with, they can try to attack your machine with back doors and spyware, or that fails they could potentially rubberhose you to force you to reveal what was communicated.

Bitmessage encrypts everything and sends every encrypted message to every recipient in your stream. Thus in theory it can't be proven whom is talking to whom. But Bitmessage has unaudited code and security model, as well it is often subject to spam which may to cause real traffic to move to more streams, thus diluting the anonymity sets. Also Bitmessage is very poorly programmed, has lots of usability quirks, and often doesn't work on some user's connection.

Someone really needs to make something better.

As for encrypting standard email the easiest way, Google can help you with that, such as PGP plugins for open source email clients. Your recipients will need to use PGP too and I believe there are easier plugins now. It is still a pita though. As I said, someone needs to fix the internet! I am working on it! But I am only one person (or perhaps a small team of devs).



Install Linux, such as Mint Linux is very easy. Abundant software often for free.

Ditch Windows. That is your problem.