Your still a victim of the markets you are in. Regardless of if the Penguins promoted from within and or had RFA or cheap players would it be enough? Your fan base and your talented core need the confidence that you are going to build around them properly, not "stagger around" trying to find the right fits.
But that is the nature of parity in this league. Other teams were willing to overpay for the better depth players because they knew teams like the Penguins couldn't. It doesn't help that the Penguins began to start having culture issues as time went on. I think it was the right move for the Pens to let go of Shero because that team needed whole sale changes from a culture perspective. Who they replaced him with however? *laughs*
Either way to me Shero has proved he has the competency to analyse a team and work around it. It helps that with the Devils he doesn't have to have the pressure of people going "we have Crosby, we have Malkin, why can't we win?" You even made that comment yourself. Teams with that kind of star power never settle for bad results, and it often leads to the pressure of thinking because you have talent like that you have no excuses. Shero will do good in New Jersey imo.