I'm not sure picking Wheeler over Laine is a real thing. Certainly it is speculative.
Letting the room fester and sticking with Maurice for too long are related, IMO. Might be considered as 2 parts of the same issue.
I think Lowry was considered as a possible future HC from the time he was hired. It did not seem like an unreasonable thing to try at the time. It didn't take very long to see that it wasn't going to work, but they were not going to fire a second HC in the same season. It was too late by then anyway.
Not trying to justify Chevy here, just critiquing your list.
I see Chevy's biggest faults as things not done, rather than things done. I don't think he has been bold enough, aggressive enough, in pursuing a better roster. This is just my opinion and is in no way provable. You can't judge what didn't happen. I think he has been patient to a fault, literally to a fault. It has helped him avoid some big mistakes while also preventing him from making any big progress.
A more aggressive style risks making mistakes that see your team finish lower in the standings. That pain is mitigated by higher draft picks. When it works, you get a legitimate window of contention and a real chance at winning the cup. Risk averse management leaves you permanently stuck in the mushy middle.
Yeah, it wasn't Laine vs Wheeler as much as it was impatient, immature youth vs the Jets establishment. In this case, the establishment was the owner, GM, coach and senior leadership group. That group was carefully chosen and, once in place, mutually supportive, slow to change and loyal. To a fault.
One thing I will say about Wheeler is that he has been incredibly loyal to the city, team and management. When he was most productive on the ice and the team was winning it was a marriage made in heaven. But loyalty can also lead to poor decision-making or indecision (your point) and that has cost the team. I feel badly for Wheeler but still recognize that his words and actions (and also silence and inaction) are part of the problem.
The whole Atlanta leadership core bought into their new city and team 100% and deserve a lot of credit for that. Unfortunately, they aged/ injured out before they could have a multi-year Cup run with the younger stars. A number of those younger stars--Trouba, Laine and now PLD have put their personal preferences ahead of loyalty to city or team. They are a new generation of me-first stars and TNSE is going to have to adapt more quickly to that reality, because they are not buying the loyalty/stability cards that Chipman and Co are selling.
There are others, like Ehlers and Morrissey, who appear to be less entitled and more willing to embrace a shared future with their NHL club. Would be nice to have a reliable psychological test to identify those types before the draft.
It's a complicated business for sure, but times and mores are changing, and TNSE has to change with them.