I think you and I both know that the Yanks will not release Jeter next year if he accepts his option.
IMO, the way Cashman is talking about Jeter and the DL now, I think he's attempting to say "YOU NEED TO BE ABLE TO PLAY A COMPETENT SS". To me, it's a message they're trying to send not only for this season but for next season also. They may give him a PR job next year making some big money so he will decline the option and both can save face.
As far as money vs. wins, that's changing. Has been for a couple of years. The H&H boys are far more concerned with the bottom line than George ever was.