There are no strategies that yield guaranteed positive results. Every credible move to win a championship comes with the risk of failure.
Tanking is advocated for on the basis that it should improve the odds, not that it gives perfect odds. It doesn't give perfect odds, and for that matter neither does keeping Weber, Petry, and Tatar until they're 40 or close to it like the Habs did with Markov and Plekanec.
The argument for tanking this year and possibly next year is that the Habs youth and prospect look like they might form a good team in the period 2022-2027, approximately. That is a Habs' team that might actually compete, and thus moves should be taken to add to that core. That can be achieved by adding good young players, prospects, and draft picks today. As an example, trading away Pacioretty yielded Suzuki, who might become the 1st line center of that credible core, at the loss of Pacioretty today.
In contrast, Weber and Petry are not expected to be productive in that period. They are productive now and probably next year, but that's irrelevant as that is for a losing cause.
I have no issue trading the likes of Petry, Tatar, etc. I understand there are no guarantees - which is exactly why I have big reservations about trading Weber, and especially Price. They are two absolutely excellent players.
I look at Weber and based on the type of player and his conditioning, I see a decline similar to someone like Chara - who even past 40 is still an impact player. Not trying to exaggerate and say Weber still be a #1D at 40 years old - but in 2022, 23, 24? Yeah - i don't expect him to decline all that quickly, and that falls right into the supposed "window" you're targeting.
Price? Same idea. I value his ability very highly - and can see him remain a top goalie in the league for many years. Clearly he is somewhat fragile - mentally moreso than phsyically - and hopefully that's something he does a bit better at when we get a better team around him.
But to come back to your suggested "window of 2022-2027" - I still feel like that team has a better chance at the cup
with Price and Weber, than without (unless we completely luck out and win a Dahlin/Matthews/Eichel level of prospect at draft - but odds of getting someone quite so high are super slim).
So yes - keep on trading the likes of Pacioretty for Suzki type returns all day long. Petry, Tatar, etc. But when it comes to Weber, and especially Price - i'm way more hesitant.
