Spending doesn't equate to winning, what it does mean is a team's core players can be kept for the long term.
IMO the question Sens management has to answer is, are the current core group good enough to be cup competitive or do some of the existing pieces need to be moved/replaced?
IMO the core group of Karlsson, Turris, Ryan, MacArthur, Spezza, Neil, Phillips and Methot aren't good enough as compared to the core groups of the top teams.
IMO there needs to be significant improvement on at least 3 of these players
The youth and mid-experienced players are more than capable of contributing to a winner.
Improvements needed on at least two and that should happen to the bolded ones as they retire soon enough.