Generally,the sharper the shoulder angle,the more likely the cases are to collapse.While I'd keep that in mind,I don't know you are collapsing anything from your pix.
Redding makes fine dies,so I would not,myself,think too hard about the dies being wrong.
I did notice your brass is dirty/carboned up.Please understand grit embeds in brass .That fact is used in industry with a tool called a lap,which can be used to cut very hard steel,such as a set of dies.That carbon is gritty and sticky.
A very good plan is to get a Lee universal decapper die,less than $15.Deprime your brass,then let the brass spend a while in a vibratory case tumbler so it is clean.
Another fine tool to get would be a Wilson(or other good brand) of bushing cartridge case gage.These are not too expensive,under $30.
While it is the method in the instructions of all the die mfgrs,bumping the dies on the shellholder is just not a good practice.It results in too much shoulder setback which causes problems.
With the cartridge case gage,you can back the die off,then gradually bring it down until the brass fits between the hi-lo limit on the gage.
Another method is the RCBS Precision mic,about$35,which allows you to control a desired shoulder setback(.002 is good in a bolt rifle).
I find the RCBS and the Dillon spray lubes work great.Apply it to the brass in a plastic coffee can or tub,agitate it to distribute it,spray it again,agitate it.I usually go about three times,the brass will have a lubed feel to it.Then you must let the brass rest a while,exposed to air,so the volatile carrier in the lube can evaporate.Thats important.
Its a good plan to run a nylon bore brush(they make a handle for them)through your case necks.It assures the id of the neck is clean,and will help spread the slightest touch of lube inside.Brushing out your necks will likely show an accuracy gain.And,your expander ball will be happier.
After sizing,check case length.Trim if necessary,but in any case,on new brass chamfer the ID and OD.Your bullets will be happier if the case mouth does not gouge them.