@Ragesoss
One alternative to having compiled CSS in the master branch would be to only commit build outputs to a "deployment" branch. This is what we do in WMF Fundraising, and I've grown to like it.

Regardless of how "binary" deployment happens, I really like the idea you bring up of supporting multiple skins. I've changed the task to focus on that goal, please feel free to revert me though.

@awight: we've already moved compiled CSS and Javascripts out of git. Compiling and uploading them is now part of the Capistrano deploy process. (How we got there: we needed to fingerprint our javascripts to make sure clients weren't getting bugs because they still had cached javascripts. Adding a deleting the huge compiled javascript on each commit got old real quick.) At this point, the deploy process usually happens via Travis, also, so that we know the build environment for the assets is consistent.

@awight: there's currently a CSS refactor going on, so it should be pretty easier to set up a skin system after that, via stylus variables. (I think.)