I don't know about octopress - I don't get who the customer is. That rake script can be done in like 15 lines of any scripting language (I wrote my own in about 10 minutes). I don't have any issues styling my stock Jekyll blog.

If you are using a static blog site over something like WordPress you are probably technical in nature and can pretty easily setup your own Jekyll site. The only benefit I see personally are the plugins - which you can't even use on Github Pages as far as I know.

IMO octopress is a solution looking for a problem.

Definitely agree with this. Octopress definitely launched with momentum but it relies on a fork of Jekyll and custom plugins.

This necessarily means GitHub can never merge any developments upstream even if they wanted to since GitHub needs Jekyll for GitHub pages.

My main concern right now is moving Jekyll forward which is a lot more frustrating of a problem since I want to make improvements that will work natively on GitHub pages. My first solution to this will be the use of a lot of javascript =), with the requirement that it degrade gracefully.

Plugin development is still worthwhile since from the replies it seems a good amount of blogs are self-hosted. The trick is to properly separate and advocate the plugin self-hosted format from the deploy to gitHub super easy quickstart format.

I can't speak for the self-hosted side of things, but two underutilized features for github hosted Jekyll blogs that I think could be really neat are Pull Requests (for comments, typo corrections, or collaborative blogs i.e. AltDevBlogADay) and the GitHub API (ability to query the files in the repo akin to a SQL database for Wordpress, OAuth with the Github sign in button, and using Javascript to create posts via commits).

The collaborative blog via pull requests seems to align with your mission of getting more technical experts writing on the web - the steps to getting a post published: write it in Markdown and submit a Pull Request. You could have an Editor comment on the post in the pull request, offer suggestions/corrections etc, then merge into the main blog repo.

Thanks for the AltDevBlogADay reference. I hadn't heard of this.

Your suggestions seem spot on. I hadn't thought to incorporate the GitHub api for collaborative features like you outline.

I had an idea for a reputation system backed by GitHub auth. Basically any githubber can upvote an article as a kind of endorsement. The idea being that a reader can trust the source content a bit more knowing it has x upvotes or what not. It's just an idea at this point and would have to work with a lot of javascript/jsonp/widget stuff going on.

But back to your collaboration suggestions, yes definitely something I'm writing down! Hopefully working with native GitHub integration will spur more adoption.