The good moves far outnumber the bad, or even the mediocre. Gorton has done a good job. "The Letter" was 3 years ago. We are less than 2 years removed from our first high draft pick.
2 years after their first high pick, the following teams were:
PIT: 4 years away, finishing .354
LAK: 3 years away, finishing .482
CHI: 4 years away, finishing .396
WSH: 14 years away, finished .427
TBL: 12 years away, finished .402
Even if we look at the most favourable scenarios, we are still 3-4 years away. We need to be patient.
PIT won the cup 4 years later. In between then they had Crosby scoring back to back 100 plus points seasons ( a third with 73 in 50, 1 119 pace), with an Art Ross and Hart added to his resume. Malkin with a Calder, a second place Hart finish, and a 100 point season. And by 2006-07, 2 years after that .354 season they were 100 point team. The next year they were Cup finalists.
LAK had a near ppg center in Kopitar (age 21-23), Doughty makes the all-rookie team before getting a 3rd place Norris finish as a 20 year old. And the next two years they finished with 103 pts and 98 pts (actually more than the cup year).
In CHI Kane and Toews finished 1st and 3rd for the Calder. Their record improved steadily every year until the cup. And it was only one year after Toews and Kane arrived that they were already a contender.
WSH: 14 years to win the cup, sure, but to be contenders? We all know what OV was his first two years even if the Caps were awful, and by the third they had their division locked up. The only thing between OV and a cup in 2010 was Jaroslav Halak, and they were serious contenders every year between then and 2018.
TBL, again, weird to go by winning cups. They made the conference final in 2011 and Stamkos had 2 40 goal (1 50 goal Richard winning) seasons as a 19 and 20 year old. They made the cup finals in 2015. They'd been consistent contenders since then. The one year they missed the playoffs, Stamkos played 17 games and they still finished with 95 points (same as the 2011-12 Kings).
Point is, all of those teams were contenders before they actually won so the 'years away thing' seems pretty skewed. You can only build a contender.
Second point is that all of those teams saw HUGE contributions from the young talent almost immediately. I am not down on Laf or Kakko but we have not seen that to this point.