Hi jay,
Contenders are extremely picky about headpace. It is sounding like you are re-sizing too much.
Casisc Contender procedure is to take a full load fired case, back the size die out, run the case up & lower the die to touch the case. Then begin lowering the die in 1/16th of a turn steps trying the case in your gun after each step. When the receiver/bbl fully locks up with a firm closing action (moderate force), your die/headspace is properly set.
If your contender closes too easy, you have a chance of excessive headspace but it should not take excessive pressure to close the action because then you are forcing the under headspaced cartridge into the chamber. Just a good firm closing action, not a massive slam it shut action.
With the proper headspace, your cart life should go up to a more reasonable number and accuracy should show improvement too.
MLG