The Penguins can still come out of the Crosby/Malkin era relatively healthy but they need to do some things very well that they haven't in 10 years. Mainly drafting the right players and developing them properly.
We are in a position now that we don't have to spend assets on rentals each trade deadline. No more Stempniak's, Morrow's, etc. We have core pieces in place all over the lineup, and free agents/current prospects can supplement the current core. So for the foreseeable future, unless some great deals come along, I don't see many more first rounders being dealt. With those, and the other picks, it can not be overstated how important it is for a good percentage of those players to pan out. The picks from 2017 to the end of Crosby and Malkin's careers will determine how good the team is when they retire. It'll either be X-Gen years bad, or they will still be a competitive team, though it'll obviously be harder since they don't have two of the best players in the league.
Until they retire though, who gives a ****! Prospects don't win cups!