He was never going to make it, there was ample medical evidence available to support that opinion. He may well have cost very little but he did occupy a place on your list that could've and should've gone to a more worthy prospect. I don't entirely agree with your view re the similarity between us and Freo re the early 2000's. However, I will say we like most teams make selection errors.
That's a harsh call on Gumbleton. He was reasonable healthy his last season at Essendon, worked hard during preseason and made our best 22 before the injury. He is a speculative trade that would seem a genius one if it worked out. Didn't cost us much in the end except maybe wasted time.