well, email encryption isn't really an option unless you host your own email (exchange) server. if he has gmail, that email will remain unencrypted on googles's servers somewhere regardless of what ever other encryption he has going on. Now there are encryption services, which allow you to send encrypted emails, typically these are part of a secure delivery service like what GE hosts; where the recipient recieves an email informing them of their encrypted email waiting for them elsewhere, and then they have to validate their ID with that website in order to recieve the email.
As for local encryption, bit locker, microsoft's own encryption program is pretty much unbreakable, and easy to use. if you want something "not" microsoft, you...