I think FSF could learn a lot from what Micah Lee is doing at the Intercept. He's been doing a bunch of articles that are a nice blend of why and how with a nice conversational feel.
In terms of outreach and informing new generations of users... I think adopting that style would be a big win. Even non-technical users have a multi-year investment in Windows, and in spite of all the polish of modern distros, the jump to FOSS is still a big one. Help people make it.