A few thingz
I don't share Jeff Atwood's enthusiasm about HTTPS / encryption. What will happen if HTTPS becomes the standard and if HTTP is considered by browsers as "unsafe"?
It seems to me that then, the web will be separated in 2 worlds: professional websites who can afford SSL certificates and a dedicated team to maintain the certification process ... and the average small webmaster who just has a shared hosting and a Wordpress. The latter will be slowly "pushed out of internet" with the threatening notice
Even with the free Let's Encrypt initiative, maintaining HTTPS requires technicity, much more than what the average webmaster has.
Result: if HTTPS becomes the standard and normal HTTP is alerted by browsers as unsafe by default, this will slowly kill amateur content, citizen-powered content.
Welcome to even-more centralized internet. Be sure Facebook and other big content providers will like this.
Edit (2018): I'm finally using LetsEncrypt too... In short,
a2enmod ssl ; wget https://dl.eff.org/certbot-auto ; chmod a+x certbot-auto ; ./certbot-auto does most of the work. More to read here.