Encrypted text messages are relatively easy to implement as the apps (textsecure/redphone - signal) in question 'stack' nicely on top of whatever they were using for SMS already.

Encrypted mails are more problematic but aslong as they are using web mail, get them Mailvelope. On android with the K9 mailclient (+ openkeychain/apg) PGP-inline is possible to use, while it's not something your 'friends and family' will enjoy.

I have a personal disdain for pidgin/adium (libpurple), but similar to encrypted text messages: Once setup OTR is out of the way of your standard IM usage and it comes down to understanding user authentication.