When comparing Middleman vs Octopress, the Slant community recommends Middleman for most people. In the question“What are the best static site generators?” Middleman is ranked 4th while Octopress is ranked 6th. The most important reason people chose Middleman is:
[Minification and compression](http://middlemanapp.com/advanced/file-size-optimization/index.html) are as easy as setting a few configuration options, and [unique asset hashes](http://middlemanapp.com/advanced/improving-cacheability/) are available to allow you to invalidate the cache of files that change regularly.
Ranked in these QuestionsQuestion Ranking
Pro Support for a variety of templating languages and preprocessors
Middleman supports lots of compiled languages, such as Less, Markdown, Textile, CoffeeScript, Stylus and more.
Pro Extensible and flexible
Middleman has a resources page full of official and community extensions.
Pro External pipeline management with Webpack
Replace your Gulp, Grunt, Bower configs
Pro Embraces Rails conventions
Middleman follows established conventions so if you know rails, you can easily pick up middleman.
Pro Easy deployment options
Pro Very easy to use
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.
Pro Lots of plugins (from Jekyll + 3rd party)
Another advantage of being based on Jekyll is default access to the extensive plugin system for Jekyll. There are also plugins developed specifically for Octopress.
Pro Based on Jekyll
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.
Pro Uses Markdown for writing
Uses the Markdown syntax for writing blogs.
Con Too much magic happens
For new users it is hard to understand what is going on and why.
Con A little more complicated than other static site generators
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.
Con Not Actively Developed
Last commit is Feb 22, 2016, Social media hasn't been updated. Dead project?
Adding a new post, for example, causes the entire blog to be regenerated.