Every year it is Cup or bust when your core is all low 30's. The good news is we have no old players on the team. Most teams have some 34+ year old types and we have none. This team is going all in over the next 3 years because that is our best window. I actually think the chances get harder each year as that core gets closer and closer to those mid 30's. You still can compete with core players at 35 like the Sharks did when we faced them in the Cup but still is less chance each year. With that said all in each year and worry about the future later.
I personally want to tank for a couple years after Crosby and Malkin hang it up. That is the way to go to build a top Cup contender. Worked for the Pens last two decade plus playoff groups. When you rebuild you go all in with no half steps. That's why I never understand people on these boards that worry about trading picks. 1st round pick for a player that helps now is always worth it to me with Brassard, Kessel, Hagelin (1st used on Perron then Perron for Hagelin). I will always be up for trades like this when contending because those are not wasting 1st round picks on rentals which I don't like. Most late 1st round picks will not even become a Hagelin let alone a Brassard or Kessel type player. So the chances are slim to even be near the kind of players we get in the deal and the one third that does takes 4-5 years to do it. The window is now so I hope to not see a 1st round pick in the next draft. I will take a Skinner type player without question over a 1st round pick and a prospect which is his reported asking price.