How can I scale proportionally into the center? For some reason it keeps going to which ever edge or vertex was first selected when making the edge loop.
You have pivot point set to Active Element and the first vertex you select when selecting a loop is the active element. To scale to the center you would need to set transform pivot to Median Point or to Bounding Box Center. You can switch the type of pivot point for transform operations like rotate, move or scale at the header of any 3D View window: