Squash a bunch of issues

Issues addressed: #68 #72 #73 #77 #79 #80.

I triaged a few more issues: #65 #76 #78.

I also worked on some server stuff. We're running a version of debian that is no longer maintained, so we should probably upgrade that box at some point. As a result, we can't install new packages, which means we can't switch to rvm+bundler. In the meantime, dependency management is very delicate.

This PR was opened as a record of tonight's work in case things start going wrong and to open discussion about the changes.

Let me know if there are any problems!

-Mickey