This is a very long post, but I wanted to capture the essence of all of the functional changes I made as part of deploying Octopress (excluding look and feel of the site). If I ever need this information again, it will be easier for me to read this post instead of sifting through a git commit log.
Heroku + Rails + Bower
Make sure to install Bower into your projects local node_modules. This is a best practice encouraged by Heroku. You should add node_modules to source control. Note that I usually take out the template extensions. These generally compile things my app doesn’t need from frontend dependencies.