We all agree that team Presidents shouldn't be out there touting "we think we are a playoff team" as this is not very inspiring for fans. We also need to keep in mind however that the prospect of being a playoff team is just enough to keep the average fan interested and enticed to attend games. Bs' ownership has been against a rebuild ever since the disastrous 96-97 season as the attendance repercussions were felt for several seasons thereafter. I don't believe a rebuild is in this team's future, so enter the retooling reference.
A retooling concept works as long as you have a solid core to continue working with (ex: 2015). With an aging Marchand, non-existent Coyle, Zacha, underperforming Lindholm, thin prospect pool and a forward lineup of fringe 3rd-4th liners, it would still be a painful retool.
I honestly think the best they could do is move one or several of Coyle, Korpisalo, Carlo, Frederic but they'll get 2nd to 3rd rounders and/or B+ prospects. Not a popular opinion, but Marchand could fetch a nice haul and I think is worth a 1st rounder and/or a A- prospect. Moving a few of the above also frees up $15-20M of cap space for UFA's in the off-season.
Whatever the case, even rebuilds aren't guaranteed and could take a a decade or more (Buffalo, Sens, Wings, etc), so it won't happen here.
I honestly believe JJ allows the Bs to spend to the cap as long as it keeps the team competitive and the building is full. I also think that ownership's propensity for tolerance on missing the playoffs will be very small for DS and Neely. It is after all, a business and these decisions are made in a boardroom.