Resources
General Privacy:
Nuts and Bolts of Encryption: A Primer for Policymakers
A very good introduction to encryption.
Tips for maintaining privacy online
Although written for developers there is good information here.
Going Dark
Online privacy and anonymity for normal people
Diceware Passphrase
The new standard in strong, easy to remember passphrases
Messaging:
VPN:
That One Privacy Guy
A comprehensive overview of VPN providers.
What to look for when chosing a VPN
One-Time Pad