the time to really fix this team was like three years ago. It's too late to fix this team imo. Even if the organization suddenly woke up tomorrow, recognized the error of their ways, and made all the necessary changes (new management, new pro and amateur scouting, new emphasis on merit over familiarity, new focus on maximizing assets and building through the draft, etc)... well, it would take about 3-4 years until they really would reap the benefits of such moves.
Sid and geno are already slowing down, the youngsters that should be about to take on prime time roles should have been drafted years ago (as we see occurring with the red wings) or not traded away shortsightedly (ie despres-- now ready to take a top four role and you trade him???), they don't have the assets or picks to get the help that is now needed, and worst of all this organization has yet to acknowledge their cronyism and overall organizational culture is a problem. Hell, the same stupid amateur and pro scouting staff is in place, and the same stupid management structure is largely in place.
The penguins needed fundamental and drastic changes years ago. by now, even if the penguins made every right move they wouldn't be a real contender for another 2-3 years, right when crosby and malkin definitively are exiting their primes.
right around the flyers series this organization was a crossroads. they could have made the difficult and necessary changes and potentially afforded sid and geno the real opportunity to carry this team to 2-3 cups. but instead, they chose the convenient way out, practically ensuring that this was just a team that got lucky enough to win a single cup.