Goodenow is definitely guilty of underestimating or grossly misreading Bettman's/owners' resolve.
1. He told the NHLPA Executive Committee that he thought Bettman would negotiate off the 24% rollback offer, despite everything Bettman had said about the the necessity of a cap. He was wrong, and it looked terrible to have Bettman dismiss it so easily. On that day Goodenow proved to the world that he thought Bettman would settle for "business as usual" and he was wildly off in that assessment. (Meanwhile Bettman looked to his constituents as nothing more than honest dealer. He'd told the whole world he had set a standard. If Bob Goodenow couldn't see that he meant it, that was BOB'S fault, not Gary's.)
2. Last night he read Bettman's statement that there would be no further negotiations and he assumed, once again, that Bettman would settle for business as usual. Again he was wrong in his read on Bettman. (And again Bettman simply looks like a guy who holds to his position. He stated that if the players rejected it, there would be no hockey. The PA rejected the proposal, there is no hockey. Whose fault is that? Bettman's for saying what he means or Goodenow's for choosing to believe that Bettman wasn't serious?)
Personally I don't see how the Association membership can look at this and have confidence. These two incidences show that Goodenow doesn't understand Bettman clearly enough to successfully compete with him. And yes, I agree that his failure to understand that times have changed is a reflection on Goodenow.