[thomasbk]

The answer to things like the Pidgin configuration issue you mentioned could be https://tails.boum.org/ -- a live USB distribution that runs all traffic through Tor, and comes with Pidgin preinstalled and preconfigured. It has optional encrypted persistence too.

[derrida]

Yes, I did show some people through this too. However, it's not usable as an everyday operating system, for, say researchers such as academics, or journalists.