@ttopham
It looks like it is your theme “pressive” that causes the problem.
I tested a few scenarios where other plugins would load the “select2” script in various ways and break functionality of Content Aware Sidebars, and I found a solution that would fix the problem in most cases.
Let me know if updating to version 3.1.1 solves the problem.
If it does not, there is unfortunately nothing more I can do, and I suggest that you contact the developer of your theme.