I also pay a lot of attention to fitting stocks to me. I have a lot of guns and rarely shoot the same gun twice in a row so I built a hot lamp bender to adjust for drop and cast. One gun may cause bruising of my cheek bone while a similar one may not. I would guess from this discussion that it may be stock pitch. Thoughts?
Have you considered that each time you bend a stock up or down, to increase or decrease the drop, you are changing the pitch as well? That may well be the reason for the bruising you experience with some of those guns.
In my experience, bruising of the cheekbone is much more prevalent when I shoot a gun that does not have enough drop. I am highly conscious of how much rib I see when I mount a gun, and will cheek a high stocked gun harder to try and make it shoot nearer flat for me. I am in the process of putting add on ribs on top of the gun's rib on a Verona 410/28 O/U right now, to cure that issue. I could have bent the stock, but adding more rib is easier and less risky. And since it's a target gun mostly I don't really mind as far as aesthetics. I may take some before and after pics just to show what they actually look like.
SRH