Switching to Pelican
I have become increasingly frustrated with octopress and its complexities. The tools I was using to maintain the blog were unnecessarily complicated for what they were doing. I was constantly looking for fixes for problems I didn't understand. Official documentation I found was just plain wrong at times. So I decided it was time for something that made a little more sense for me.
I switched to Pelican which is a python based static blog generator. There are a couple of oddities I have noticed which I am still trying to work out. Weird CSS rules that apply to page elements that don't make sense. It is also much easier to setup. Now if only I could figure out how images and plugins worked but that will have to wait till the morning.