Hamilton is soft, glad he's gone. Seguin was a bad, bad trade. What did they expect? The kid was a 19yo millionaire with an overactive libido. He would have been worth keeping and letting him grow up.
Debrusk was a playoff stud in Juniors(as was Marchand). Since Cassidy's removal he looks like the kid from year 2. That Kadri hit knock him back quite a bit, but he seems to be back and better than ever.
Your concerns aren't unfounded, but under the conditions of "one last ride", you HAVE to go for it.
I don't think we will be as bad over the next 5 years as some. Especially with that D and goalie tandem. Pasta, Debrusk, Zacha, Frederic, Coyle not so much for his price tag. If we get Bertuzzi and Orlov to resign and back fill with good young bottom 6 for checking. We should be competitive.
Outside of 2019 we've been just another good, not great team.