The LEE decapping stem is designed to slip. Needs to be tight.
I've used the universal die for thousands of rounds without breaking a pin.
Normally the pin will enter the flash hole first, align, and then push out the primer.
Any misalignment and the pin hits the web and bends/breaks.
Putting force on the pin when it is not in the flash hole will damage it.
It's a 'Feel' thing when operating a press.
When decapping is combined with another operation, like Full Length Resizing, decapping 'Feel' is lost. I haven't done crimped primers in a long time but pin in the hole and a slowly applied force should suffice to decap crimped primers.
Loading for precision, not bulk pew pew pew rounds I tend to separate every operation.
Takes more time but when 'Feel' is needed, it's there.
Sometimes I touch the base of the case so I can actually feel the pin enter the flash hole before pushing.
My typical reloading process (some order in steps is variable) is;
Shoot,
dump spent cases into tumbler,
take a nap

,
remove cases from media and media from cases,
quickly inspect cases for any visible issues,
anneal some loose pocket cases then anneal like cases,
deprime with the universal die and 'feel' for loose pockets,
Body size with a Redding Body only die,
-I have one preset for my 22 Nosler/Dogtown brass in my No-Gas AR, and another preset for the wife's
22 Nosgar Gasser. Run a few and check bump with a fit check in the chamber.
Check length and trim (sizing can change case length),
deburr and chamfer,
Neck size with a LEE Collet Neck Die,
Sort the pile of brass by weight,
Presort bullets by weight and length, base to ogive,
Prime, again feeling for loose pockets,
Set the desired quantity in a loading block neck down,
Weigh powder and charge case, insert an upside down projectile in the neck and set back in the block neck up,
Seat bullets and check CBTO for a few then run with it.
Wipe off all lube and if for a competition fit check every one in the corresponding chamber.