The most surprising thing to me in the OP was seeing that Octopress users had been updating their sites all this time...I frequently checked back on the Octopress blog, and then the Git repo, to see how to go about doing that. I tinkered around playing with the dev branches but didn't know enough to get around their hiccups. Finally I gave up on it and just went to Jekyll, which was definitely a blessing in disguise, as it let me figure out more of the process of static site building, with fewer abstractions and conveniences in the way.
I don't know if I'll ever go back to Octopress -- I'm a devout Middleman user now -- but the direction it's taking seems to be the right one, and I'm amazed that the author, these past few years, is still cranking away at what could easily just be a legacy, soul-sucking project -- given the size of the userbase and the number of dependencies/upgrades involved in changing the code base.