Even simpler, if the case has one hole in the center of the primer pocket, its Boxer primed. More than one hole (and offset from the center) its Berdan primed, and NOT reloadable with common US components and methods.
The ironic thing is that the Berdan system was invented by an American, but became the standard used in Europe, and the Boxer system was invented by a European (English I think) and became the standard used in the US.
Shine a light into a fired case, and see how many flash holes there are.
Since you've done 150 and only bent one pin, I'd think they were boxer primed, and you problem is some of the cases could have offcenter flashholes, or holes that are smaller than your decapping pin.
Generally I'm not a fan of LEE products, but they make a decapping set that is a punch and base and very rugged. And if you bend or break it, Lee will replace it. If decapping military brass for the first time, get and use the punch and a hammer, and decap the case. Slow and tedious, but absolutely effective. Then run it through the sizer die. Then remove the primer pocket crimp (either an annular ring or the stab type crimp) normally used on military ammo by either swaging or reaming the pocket. Doesn't have to move/remove much metal just enough to allow a new primer to be seated.
(this is not the same thing as "primer pocket uniforming", though there are tools to do both)
The Lee decapper and base sets come in 2 sizes, one for .30, the other for .22 calibers. I've been using the .30 cal one since the 70s, and while the head of the shaft has become somewhat mushroomed from hammer blows, the decapping pin is just as perfect as it was when brand new.
Takes a little practice, but you'll quickly get the feel for when the pin enters the flashole, then a few wacks and tis done! Do have something handy to clean up the ash with, though...