I think anybody honest with themselves will acknowledge that high picks are far from a guarantee. But personally, I'd sooner take 9 years of no playoffs and one championship, than 10 first round exits,
The Wings won a Cup 9 years ago, though, so I fail to see how you're adhering to even your own heavily weighted declaration given that Detroit's done far better than what you allege you'd have been happy with, yet are still demonstrably unhappy.
Even assuming you've forgotten their Cup, your example is poorly designed because the give or take isn't remotely realistic or repeatable. We know this because the last 25 Cups have been won by 13 teams... meaning that 17 current teams haven't won a Cup in a quarter century, and 23 teams haven't won in a decade.
So, heck yeah, if the trade is 'only' missing the playoffs for 9 years and winning 1 that'd be a great bargain.
In other words, you'd have to BANK ON lightning striking several times - with odds even lower than the rate of success for high picks - for "rebuilding on the fly" to ever pan out.
You will continue to struggle with a competitive reality as long as you equate 'working out' with, and only with, winning a Cup. If you elect to strip yourself of all ability to perceive nuance in success, you will be endlessly frustrated with what results save for those extremely rare, generational at best flashes.
If that's what you want, hey, great. Seems like a drag.
For example, I'd be thrilled to be a Leafs fan right now, and they might not even make the playoffs.
Sure,
right now. That's always the amusing part of all of this super-standard-itis. You want to experience all the success, and then fairly soon after the success even just moderates to something above league average the demand is 'why can't we be like that other team that hasn't had success in half a century, now?'
And just imagine if, like most of the NHL, the Leafs top out as a first or second round and out team... a level of success that sends so many here howling into the dark in terror?
There are 10-15 teams that I'd say are making good decisions, regardless of their position on the cycle of success. And when you're approaching half the league, I don't think that expectation is unfair to have for the franchise you root for...especially when said franchise had previously set the bar for both success and decision making for a very long time.
Seems like you're moving the bar here. Now it's just 'good decisions', when I thought the One True Standard was winning Cups?