I just purchased a Winchester model 1100SS, now I know it wouldn't be easy to cock considering it's a break barrel, but will it become easier over time or will it always be particularly stiff ?
No, they don't get much easier. You may get stronger if you do it enough and it may seem lighter, and it may get smoother as the gun breaks in, but if the actual cocking effort does drop off significantly, it's not a good thing. Means your spring is wearing/worn out.
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