Call it brilliance or idiocy, but I have figured out the easiest way to win a Stanley Cup.
All you need is one or two superstars and role players/contributors/solid d/ and goaltenders. So pretty much let's use Calgary as an example since we have some pretty good pieces but haven't been past the first round in a while.
All you have to do is schedule your signings so that 75% of your team is on a CONTRACT YEAR during the year when you wanna win a cup. It's a fact that players on a contract year play 1.5 times as good as they would regularly. Look at Kolvachuk trying to get his 100 million dollar contract, he's averaging more than a goal a freaking game! Same with Mike Cammaleri last year with the Flames.
So there you have it. If 75% of your team is on a contract year you will win the cup because everyone will play their hardest to earn their payraise. You are definitely screwed the new few years but you always have a five year period after winning the championship where no fan can question the organization or complain about how shitty your team is.