When we left monobook behind (or were forced to, depending how one looks at it), we lost some features that really aided in navigation. Most notably, we no longer have nested navigation menues in the left navigation bar. This means we need to redesign Mediawiki:Sidebar
to do what we need. I'm sure there are css or java fixes that can be done to add extra features to the existing skin, so I wanted to open a discussion on the issue here.
While searching for an existing shoutbox extension, I came across this site:  that has a design similar to ours that I thought we might look into emulating. I especially like their navigation bar and the table headers on their main page. Overall, it's a really simple, elegant way of organizing a wiki without all the bells and whistles wikia employed to do so. I'd like to see us get something like that implemented here as a way of distinguishing this project from the wikia one and giving us a leg up on the "easy to use" and "looks cool" fronts.