Hal is an enormous part of the equation and unfortunately for Yankee fans the equation doesn't work all that well.
He supposedly is very fond of Cashman so it is unlikely that Cashman leaves before he decides to retire (could be 15-20 years from now). Additionally, if Cashman were to decide to retire earlier, Hal would almost definitely hire from within and promote one of the staff who is fully aligned with the current (metric heavy) philosophy.
What bothers me most is that we currently are operating under the premise that we will be financially responsible, except for when we are not. We couldn't add contracts at a number of different times over the past few years yet we also grossly overpaid Cole and recently took on $50 million to get Donaldson for two years. I don't get the decisions when it somehow is acceptable to add ridiculous salaries when instances where adding salaries are dismissed even if it could help us.
Cashman did a masterful job six years ago, shedding older players and going into a full rebuild, getting us back to being highly competitive two years earlier than what could have been reasonably expected. Everything that has happened since has moved us sideways or backwards.