Been using octopress for a little over a year now, and this post sums up everything thats been a pain in the ass for me when it comes to upgrades/customization/etc.
I hope, however, that the author gives some thought to being able to freeze content, perhaps at the plugin level. I would hate to use a plugin, generate output, and find that at some point in the future, when the gem hasn't been maintained, the rest of my site suffers because I'm no longer able to mix current code with a plugin used at some point in the past. It would be great if I could have some sort of 'freeze' functionality that would take all the plugin level output as it exists today, lock it down, and update the rest of the site without having that plugin installed any more.
You can specify a specific version of a plugin in the Gemfile and it will never change, but you'll be able to update everything else.
I look at GitHub issues and I'm just afraid to mess with things. Even if I fix stuff, there's a high likelihood that it will break something else or be hard to update to. I too cannot wait to release this.