Factors affecting Cheek Weld?

Setting up the rifle to the shooter is an important part of it.

Length of pull is one thing

The cheek piece / stock pad is to line the shooter's eye to the ocular of the scope. Having the scope mounted correctly for the shooter, via the proper eye relief is another fact. Many don't understand this and will, "Hunt" for the proper sight picture becaues the head is not lined up correctly.

Better rifles have more adjustability, that adjustability to bring the rifle / scope combo to the shooter versus the shooter having to adapt to the rifle. Think of your car and moving the seat and mirrors to fit you. If someone moves the seat and/or mirrors you'll likely notice it.

Here is a great example of a student taking a stock Tikka T3 and making it fit him SH_HD_TikkaStock-1.jpg
 
A long time ago, my dad, an accomplished competitive rifle/pistol shooter, drilled into me time and again, that direct bone support was paramount to a good shooting position. Every time you need to use a muscle to move the rifle into a position that "centers" your shot or "makes" your sight picture, you inject a variable into the shot you cannot reliably or consistently repeat. Your bones/skeleton is the only rigid portion of your body. The more relaxed your muscles and natural your position, especially in regards to that 8-10lbs weight at the end of those relatively small neck muscles, the more your bones are making the position and thus the shot ... and the more consistent the shot will be.

As for the picture above, I remember seeing more than one McMillan M14 stock at Dam Neck with all manner of ammo crate foam, EB Green (rigger's tape, 150mph tape, duct tape, whatever your group called it), even some really well-done fiberglass add-on cheek-pieces.
 
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When your rifle is properly adjusted, or modified to fit you, and you consistently assume a proper position behind the rifle, your face should make contact with the stock in exactly the same way, and in exactly the same place, every time. Even the pressure applied to the stock, by your cheek, must be consistent. I can usually tell when my position is "off," because my cheek weld doesn't feel right. This is a similar principle to the archers anchor point. I'm not crazy about stock packs, or any addition to the comb of the stock that is too soft, has the possibility to shift position, or must be removed for any reason. This is why I prefer stocks with adjustable cheek pieces. They can be easily fit to the shooter, and marked so that they can be returned to the optimum position, should the need arise.