Two posts with Wordpress was enough for me. There are a few complaints I have that discouraged me from investing more effort in a Wordpress blog:
Uncomfortable editor. I do not want to write text in a browser textarea; I want to use my favorite editor. There is a great project out there trying to bring it to the web, but any web editor will have fundamental limitations, particularly when it comes to loading configuration and plugins. Anyone who suggests copying back and forth must have never tried it---it is an unnecessary hassle.
I do not want my editor to have a bunch of distracting elements cluttering up my screen and distracting from my writing.
I want to be able to write in Markdown. Everywhere. The first plugin I tried would not store the Markdown I had written. If I had to come back later to fix a post, it would try to translate the generated HTML back to Markdown. The Markdown it generated did not match the style I write, which I found annoying.
The second plugin did not have this problem---it had a different one: no support for Markdown in comments. I want this blog to serve as a place for rich discussion, hence having comments at all, and like I said, I want to write Markdown everywhere. (I expect software to be the primary topic, so I also want syntax highlighting everywhere.)
Comments. Even looking past the lack of Markdown and syntax highlighting, the comments are unimpressive. I specifically want authentication to connect identities with ideas and opinions. I could install Disqus on Wordpress, but dealing with Wordpress plugins always seemed to leave a bad taste in my mouth.
Black box. I do not know exactly how Wordpress generates my pages. If there was ever a problem, I would not be able to troubleshoot it quickly or by myself. My posts are locked away in a database. Trying to edit the colors, fonts, layout, or other visual aspects proved to be a painful experience with primitive tools (and none of the freely available themes suited my taste).
In summary, the greatest feature advertised for content management systems like Wordpress---a layer of abstraction that protects authors from the details of MySQL, Apache, HTML, and CSS---is not a priority for me, and its implementation in Wordpress is too clumsy.
Jekyll addresses these concerns, and I have spent the last week creating this site with it. I had briefly considered Jekyll when I first created the blog, but I thought it would require too much effort to get going and that Wordpress would be good enough. I was right. I am not sure I would have ever finished my first post if I had made myself use Jekyll in the beginning, so for ease of installation, I have to give praise to Wordpress.
That said, Jekyll brings a few advantages I did not consider before:
Automatic back-up. I work locally, giving me an extra copy of my site off the server. I also use Git, which does version control better than Wordpress and lets me easily push copies to other machines.
Security. I was never really concerned about this, but I figure it deserves a mention. There is no web-accessible administrator panel to hack.
Using Jekyll has been quite a learning experience. I discovered an abundance of information on the web covering every topic and issue related to web design, and it has been somewhat overwhelming. I feel that the topics are perfectly suited for a course format and would benefit from a better balance between breadth and depth. Even though I still need to do some reading and catching up, I want to give it a shot. I have a structure outlined; I just need to make time.