Winchester brass = crap?

I use Federal and Winchester brass. I find that my Winchester brass tends to die more often in my press and suffers more after firing injuries then my Federal Brass. But my rifles isn't fond or Winchester factory loads as they tend to get hung up when I'm trying to close my action more often.
 
If I understand the concept, excessive headspace in this case would mean the case is too short for the chamber, causing the brass to stretch more than it should. What about shorter .38spl brass?

You understand the concept. One detail is the definition of "length". Headspace is defined as the distance between two specific points in the chamber. In the case of .38/.357 chambers, that distance is between the breechface (recoil shield of a 686) and the extractor lip. In other words, the cartridge is supported on the front and rear surfaces of the rim.

When fired, the hammer blow will force the case forward until the front of the rim hits the star extractor. The cartridge will fire, the case will obturate, then the head will be forced back until it hits the recoil shield. If your rim is too thin, the distance the head will be forced back will be excessive, and the case will neck to accomodate the elongation. My books show the required rim thickness of .38 Special /.357 mag/ .357max as 1.48-1.52mm.
 
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