I recently discovered Octopress, and after some investigation discovered that I was basically working toward my own very similar version of Octopress. Rather than travel further down a road already travelled, I am switching over to Octopress. I plan to port some of my extensions over (and in the process switch Octopress to use ejekyll), but this will let me focus more on getting content into the blog rather than spend too much more time messing with the site generation. Hopefully I’ll start blogging on a more regular basis.
I’m also switching to Heroku for hosting. The code for my site is private, allowing me to store more sensitive information in the configuration and automate things like Flickr integration which require a secret key. Publishing is really simple - I just push to my heroku repo and the site is live. Very simple. I like it.