Some boundaries pass along the centre of the feeder roads therefore in terms of housing one side of the road reaches the boundary before the other. I couldn't therefore tell you where the correct place for a sign should be, they are usually placed where they are most visible without causing obstruction or distraction from a safety signs. Going by my work area (in NEDDC) doesn't help as my boundary on each road is the mini roundabouts which are well outside Chesterfield.
JR is right about the one coming from Winsick not being there, the one from Grassmoor is there but needs replacing.
Not sure why we missed out on Destination Chesterfield signs, must look into that.