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As Octopress is simply a framework on top of Jekyll, it benefits from being based on one of the most popular site generators available. The primary benefit is that it is backed by git and is built in such a way that the site can be easily re-generated if the content changes. See More
Octopress is designed to remove all the time-consuming and frustrating tasks you usually have to deal with when using Jekyll. You don't have to write your own HTML templates or do any configuration to get started. The default template also takes care of any basic CSS/JS you need to write to get going. See More
Middleman is a big piece of software, it's not simply a static blog generator. Because of all the functionality and flexibility it offers it can be a little more complex than other static site generators and a little harder to learn all of its bells and whistles. See More
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