This photo in particular leads me to believe that the very outboard corner of the roof is just too high, maybe even as much as 1/8". Sometimes I use a flexible aluminum yardstick held above the area in question and bent to various contours in order to get an idea of what's going on and how it can be addressed. It appears that filling would require extending the fill out over a foot away from that corner to achieve a visibly pleasing contour.
As always, pictures can be misleading, but that's what I see.