Not every team doing bad as often as Canadiens in late first pick and 2nd pick. If you're happy one good year pick every 10 years, I desagree.
Timmins track record for 1st round picks when we don't make the playoffs:
2004 - Chipchura - bust
2005 #5 overall
2006 - Fischer - bust
2007 - Pacioretty - success
2008 no 1st
2009 - Leblanc - bust
2010 - Tinordi - but
2011 - Beaulieu - bust
2012 #3 overall
2013 - McCarron - bust
2014 - Scherbak - success
2015 - Juulsen - success
2016 #9
2017 - Poehling - too early to tell
I think he's redeemed himself with Scherbak and Juulsen. He's 3 for 9. If Poehling makes it, he'll be 4 for 10. Some will argue it's too early to tell with Scherbak and Juulsen. I'd be shocked if Scherbak isn't top 6 and Juulsen isn't top 4. 3 for 9 is probably about average. For example, Nashville has only had their 1st rounder four times from 2003 to 2015 when they didn't make the playoffs. They're 1 for 4. Their only success was Radulov at #15. It's too early to call for 2016 and 2017, but if Tolvanen makes it, they'll be 2 for 5, the same percentage as us if Poehling makes it.
As for his 1sts when don't make the playoffs, he's killed it, going 4 for 5.
2003 - Kostistsyn - bust
2005 - Price - success
2007 - McDonagh - success
2012 - Galchenyuk - success
2016 - Sergachev - success
I did a similar analysis with 2nd round picks I'll look it up and post later.
I think people focus on the busts too much. There will be more busts than success for late 1st round picks.