Interesting question.
I championed trading Karlsson immediately following his playoff run, knowing the rift between he and Melnyk would result in his departure at the end of his contract. Dorion did get a haul for him, but I'd like to think that trading a top 3 player at his peak (with a slight injury concern to be fair) with term at low dollars would have brought in resources that would have prevented a bottom out for 5 years. I truly think I could have timed that trade better and beaten his performance.
I also championed pre-empively trading Mark stone when he had 1 RFA year left, knowing the writing was on the wall. We would have gotten significantly more in return for him.
I didn't mind the Brass - Zib swap in principle, but hated the draft picks involved, so that wouldn't have gone through. In fairness to Dorion, I liked the Brass addition at the time, and was lukewarm on Zib. But we'd still have him if it was me.
And I'd have been less inclined to pick from the waiver wire, and more inclined to philosophically bring up talent in a non-basement dwelling environment.
So from a standings perspective, yes, I think we would have been better, without the bottom out. I'd give the edge to Pierre in drafting and development, that's his thing. PR wise, I'd have been better without question. Fewer (zero) girlfriend references, self doxxing moments, and showing of cards.
He could still fumble his way into a contender as the years go by, while who knows what heights my team would have reached. As I said, no bottom out though.