I don't get it.
Organizational culture is important, but you can't craft an organizational culture of winning when you are constantly losing. You can bring in "winners". Let's say, for example... Jordan Staal, Brian Bickell, Tuevo Teravainen, Markus Kruger, Joakim Nordstrom and TVR. You can promote guys to high positions in the org who are lifelong "winners". Let's say, for example Rod Brind'Amour to Assistant Coach or Ron Francis to GM. You can yell with all your might "Let's get out there and win!"
At the end of the day... You gotta win on the ice. Nashville is struggling if they aren't making the Playoffs. It doesn't matter how many "studies" they have done on welcoming fans.
As for all the arena improvements, trainers, scouts, etc... Dundon has talked about the planned improvements at every turn. He is personally invested in making the fan and player experience better. He has already started by making tickets significantly cheaper with special deals. He is doing a lot behind the scenes to put out the thousands of small fires left burning by PK.
Seems like 99% of what you are describing is already taking place. Not hard to see if you look.