The solution to this problem was actually outside of the view detailed here. The caller of the interface was being double instantiated on accident, thus nulling out the reference to the previously created NSView. After correcting that concern the app draws and works just fine.
With regard to dragging, I just implemented a subclass of NSView that implemented the Cocoa draggable protocol and added it as a subview to this parent class. That allows dragging onto the currently established NSRect that contains the menubar icon.