Even if next year is a reloading year and they don't make a deep playoff run, the pipeline of talent looks mighty impressive with solid, complimentary players (and in TT's case, gamebreaking talent). When Ben Smith is rated as the #15 prospect here, and looks to be a sure fire NHL player it certainly says something about the organizational depth. Assuming Toews and Kane are resigned, I don't see this team missing the playoffs for quite a while.
I was critical of Bowman after the last deadline, but it seems like he has a very good long term perspective for the organization. I think he's earned a longer leash, so to speak.