Look at the necks of your brass how ballooned it is. Head space is off.
"Head space" for a belted case, or a rimmed case, has nothing to do with the location of the neck or the shoulder. That is the distance from the closed bolt face to the forward edge of the belt or rim. But you are correct - in OP's first picture, sure looks like the case shoulders have been pushed forward, in that chamber, when fired.
Is typical in a Weatherby case and chamber for the outside shoulder and the neck junction to be "rounded" - not "sharp edged" - was Roy Weatherby's "double venturi", I think he called it.
If the case shoulders HAVE been pushed forward as much as shown in first pictures, would think that would be visible to the eye - simply by standing a fired and unfired case side by side on a flat surface - perhaps with some lined or graph paper behind to see any difference in length.
For cases that DO headspace on their shoulder - like 30-06 or 308 Win - is usually defined by SAAMI as a theoretic diameter - like 0.400" along the shoulder, then the shoulder angle defined versus the centre line. Is not the "whole" shoulder face in those rimless cartridges that sent head space - not the point of the neck to shoulder junction, and not the "point" of the case shoulder. But this belted case does not do that - a "headspace" gauge will only gauge from bolt face to forward face of the belt recess in that chamber. The assumption is that the reamer was ground to spec - when it is advanced far enough to create correct "head space", the grind has created a case shoulder and, usually, the neck diameter and a throat diameter that is appropriate for that cartridge. Maybe there are reamers that cut the case body area and then a separate reamer is used for the belt - if so, I have never used them.