I think we'll be a playoff team for at least the next 6 years (including this one). After that season Scheif, Little, Wheeler, Helle will all be UFA and our team control of Morrissey, Laine and Connor will be over as well. Ehlers will still be under contract so at least we have that. Also some of the young guys could decide to commit long term and not Trouba us.
After that who knows. Hopefully we'll still be good but that really depends on the guys drafted in the next 3-4 years. Who is the 16 year old kid that makes or breaks us?
I do think our best chance at a cup is this year or next year. After this year our RD is going to take a hit and depending on bridge deals we may start having cap casualties. (Matty P, Kulikov, Myers, etc.) Can the steps forward from Laine, Connor, Ehlers, Niku, Lemeiux, Appleton, Lowry, etc make up for that loss. (I think they can.)
Trouba is the real problem. If we keep him next year to maximize our best chance at the cup we could also bridge Connor and Laine to try to really load up one more time. After that I think we'll still be good, but will be on the way back down a bit, still a playoff team but maybe not a true contender. It depends how the holes in the back end are filled. We do have some promising guys coming, but will any of them be a top pair RHD and who replaces Buff when his contract is up?