Simple for me. A broken franchise should have a management team in place that can right the ship in 3 years and make them reasonably competitive in 5 years. I think that's been accomplished. Then it's maintaining the competitive team for as many years as possible. The rest is pure NHL PO chance/luck/good and bad fortune. Once the competitive team is built, it's all random bullshit.
I know all the experts here on HF and out there in the media pretend otherwise but you observe the game long enough and you see the Minnesota North Stars make the finals in '91, you see the Habs fluke their way to a cup in '93 etc. One thing that will increase the odds of forever not winning the cup is constantly swapping out your management team even if they actually put together a top 6 in the league team. So HF experts keep following Noodles/Kipper/ODog/Hayes advice