Oh, I agree that it's harder than it seems at first. But I think if you guys fully committed to pulling the pin and traded Weber, Petry, Tatar, Shaw, etc for the best package of futures you could have gotten, you would have tanked just fine.
There is absolutely a luck quotient, but sometimes you make your own luck...like Columbus passing on the consensus #3 to take Dubois. Like the Leafs taking Marner at 4 despite all the media noise about him being lighter than a stick figure drawing (Lawson Crouse was ranked higher than Marner in a number of mocks ffs). Yeah, sometimes you just get unlucky with the year you suck during (though I'd argue that Edmonton ruined Yak moreso than he was a bad pick or even a bad #1...how the hell is your best season as a pro your 18 yr old rookie season?) and rebuilding shouldn't be looked at as a one and done. Did the Leafs get fortunate to pull Matthews-Marner-Nylander in 3 straight seasons? Absolutely, but all the bad teams from that period pulled good building blocks out of the top of the draft.
-Winnipeg got Laine-Ehlers-Trouba-Scheifele-Morissey-Connor out of being bad a bunch of years in a row (with Connor the only pick outside the top 13 of the bunch)
-CBJ got Dubois and Werenski (as well as RJ that they turned into Seth) and Ryan Murray (that easily could have been Morgan Rielly instead of Murray)
-I don't think I need to get into what Edmonton pulled from the top of the draft.
-Vancouver has pulled Pettersson, Hughes, Horvat, Juolevi (could have been Tkachuk or Keller) and Virtanen (could have been Nylander or Ehlers)
Basically every team that has done a bit of extended tanking (whether they were trying to or not) have pulled legitimate building blocks that a contending core can be built around. Those who drafted better, have pretty clearly done better in that process, but all of them have walked away with the type of pieces you need. Montreal really needs 3-4 years in that wilderness.
Yep, and praying for that kind of luck is a tough place to be. I know, I watched it for a decade in Toronto.