Thunderbird Email with the Enigmail plugin (uses GPG) and is an easy to use, cross platform key management solution.
Great post Keith.
It's worth remembering that encryption done badly can be worse than not using it all. I'd urge people who want to use encryption to read and understand as much as they can when using encryption as there are many pitfalls. Key security is a biggy - the only cases of LE breaking encryption that are known to have occurred has been by obtaining private keys and passphrases. The use of open source security software is very important too in my opinion. You just don't know what proprietry software is doing when it comes to encryption.
However, the more people that do use encryption the better - I'm reminded of a comment from Phil Zimmerman about unencrypted email being similar to sending a postcard, encrypted mail being analogous to a letter in an envelope. Both can be intercepted and read, but a lot more effort needs to be expended to read the letter. The NSA will keep encrypted communications indefinitely, and they will be able to retrospectively "steam them open" in the future. Perhaps you could include PFS and OTR in your upcoming posts on this subject.
It would also be great to see some information on anonymous browsing via Tor (this is now fairly easy to set up - I posted this via Tor) and darknets such as I2P if you have the time or inclination.