This site came up in February 2009, and has been running the same version of Wordpress (unpatched obviously), with an old theme from Neoease. A slightly hacked up version of the theme is still powering Diskwave website.
To say that this blog needed to be refreshed, is an understatement. The blog looked so ugly and I was so ashamed of it, that I pretty much stopped writing for it.
My motivations for switching to Octopress are the following:
Responsive design. Most people read blogs on their phones or tablets. Having a website with a hardcoded sizes optimized for the desktop is no longer acceptable in 2013.
Static deployment. I never really understood why I needed to run dynamic code to serve a blog. I chose Wordpress back in 2009, because of its widespread use. I was not aware of the existence of Moveable Type at the time.
Use GIT and Markdown files, instead of some clunky online editor storing data in a complicated MySQL schema. Hopefully this will make my next blog migration much easier.
No comments. This was probably the only dynamic feature I used. It was hassle to maintain and keep spam free. Direct contact via twitter and optionally linking to your own blog post is a better way to provide feedback.
Ok. There is one dynamic feature I had in Wordpress, and that I am now lacking: Search.
At the moment, the migration is not completely finished. Some pages are missing from the site and I use temporary DNS redirections. Things will probably change a lot in the next few weeks.