On the flip side, I think some teams grip their prospects too tight for fear they'll one day be uber-mega super stars (let's be honest, we all view our own prospects as if they'll one day reach their full potential, haha)......while maybe overlooking the fact that even if those prospects hit their full potential, it might be well after the talent on your roster has faded from prominence. Meaning you're just mediocre now, and mediocre later.
GH for instance dealt away Byron Buxton in year one to acquire Ian Kinsler.....Buxton, is an elite prospect but he wouldn't have helped GH any of the last 3 years, meanwhile Kinsler has played a role in GH finishing 1st, 2nd and 3rd the last three seasons.....HP similarly traded away Buxton, Sonny Gray, Wacha, etc...but it enabled him leap from 2nd worst, to 2nd overall and take a couple real concerted efforts at a title....
You kind of have to nut up, pick a direction and then be willing to go all in whether it's to win now, or swallowing that hard pill to trade away a Felix Hernandez or a Miguel Cabrera, because you think it's best for your team in the long run.