For VPN I use [Private Internet Access][0] it has access points in ~20
countries (include multiple in Canada). They also provided amazing
documentation on how to setup in virtual every environment. There is
also TunnelBear[1] which is a Toronto based company and has limited
Linux support though OpenVPN[2].

As for PGP Email tutorials I would suggest the EFF's [Email Self
Defense][3] guide. It's the best.

Also if you are becoming a "tin foil hat" type you should checkout
Tails[4]. It's a Live Linux OS that aims to "preserving your privacy and
anonymity" on the Internet.

[0]: <https://www.privateinternetaccess.com/>
[1]: <https://www.tunnelbear.com/>
[2]: <https://www.tunnelbear.com/blog/linux_support/>
[3]: <https://emailselfdefense.fsf.org/en/>
[4]: <https://tails.boum.org/>

--
Have an awesome day, and happy open-sourcing :-).

 Myles,

Thanks for the links and advice! I'll look into Private Internet
Access. You're not the first one to recommend this VPN
provider (and another poster on this thread [David Collier-Brown]
linked me to an article that recommended it also). If they have
good documentation then that will help immensely. I do connect my
laptop to my work VPN regularly so I'm hoping it won't be too
much of stretch to do this for myself too.

Another question: is there any hit to the speed of the network if
I'm using a VPN? I've seen a drop in download and upload speed
when I'm on my work's VPN versus when I'm not.

As far as becoming a "tin foil hat" type, I guess we'll see... :)

Brad