Switch to O̶c̶t̶o̶p̶r̶e̶s̶s̶ Pelican
(Update 2014-11-03) I liked the Octopress concept a lot but since it used ruby so much it was hard for me to customize or deal with any issues that turned up (I don’t know ruby). Also, I didn’t like the fact that every site you want to use with octopress is a clone of the repo. I switched from octopress to Pelican, which is python based. I found it much easier to understand and maintain. The plugins make sense and I was able to make my own modifications to plugins and themes after using it for only a short period of time. Everything I wrote below about reasons and advantages of switching from wordpress to static site generator still apply.
I recently changed this site from Wordpress to Octopress. Wordpress was getting to be a hassle to maintain, especially with needing to worry about constant security updates. I think I actually had the site hacked once and I had to rebuild the site to get it cleaned up. Then you have to keep a security plugin ... I just got tired of maintaining it.
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