How are things in Detroit? I grew up there.
Winchester made several rifles which were chambered for the 32 WS or Win Special cartridge. Which model and configuration do you have? The two rounds are almost identical in the ballistics. Take a look at the Winchester Ballistics Calculator and you will see that for identical bullet types and weights (power point and 170 grain) with the rifle zeroed at 100 yards there is only .6 inches of difference at 250 yards. I have never heard of the 32 WS wearing out early. All bullets are undersized relative to the rifling diameter otherwise the bullet would not travel down the barrel.
I am not sure what you mean when you say the rear sight "chewed up your thumb". I think that if you were to shoot identical ammo types from identical rifles chambered for each you would find they shoot extremely similar with regard to accuracy. The limiting component is typically the skill of using iron sights at long range. The elevator on these sights are cut or notched at fifty yard intervals starting at 50 on the lowest notch.