I too will not buy any winchester ammo, I have had pretty crappy performance from it.
The brass seems ok as long as it is older and I can inspect it. Usually range pickup brass. I have a bunch in 45 acp and it seems pretty decent. I have about 80 pieces of 308 that is range pickup. I cleaned, inspected, annealed and sized the brass. So far it seems ok. I am beating it up in my AR10 and will toss it when it get questionable.
The brass you have looks like crap! I would be returning that bag asap. If I paid for 50 pieces of brass, I want 50 pieces, not 47 or 48. That stuff looks like a monkey was running the machines.
Like another suggested, I would look for some better brass. Lapua, Norma, hell even federal would be better than what you have there.
I would also check out hornady. I bought a box of loaded ammo and after firing, I weighed each case and measured the water capacity of them and was surprised when the results I got was more uniform and less variation than my lapua brass!