How do you use these things in the wild? Privacy stacks generally require that they are installed on both ends of the message. Trying to get my friends and family to exchange encrypted texts or OTR IMs is basically impossible.
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.