I agree it is not a slam dunk. These things never are, even if you have 1st OA. All you are ever doing is going with the best odds, the best chance. I guarantee you they will be able to make a choice that Chevy feels comfortable with. If by 'clear cut' you mean so clear that there is no dissenting voice in the room then probably not but again even if you have 1st OA there is likely some disagreement.
You are making a logical case for taking an option that I don't think exists. Huge IF it did exist then it would be a good option. I just don't think it exists. I don't think the tiers are that big at that level.
And your option requires a trading partner who has that kind of a combination of assets. As it happens this year that exists but it gives only 1 possibility of doing that deal. That 1 partner is not going to be willing if the circumstances you describe exists. They would know just as well as we would that 8-13 are all equal. I believe that if your strategy involves pulling the wool over another teams eyes it is doomed to fail before you even start.
Unless your proposition involves either the current Boston GM or his predecessor.
Edit: answered before reading all the way to your last paragraph. I agree it has been covered. There is no absolute right or wrong answer.
IF all the stars aligned then I would agree with your hypothetical proposition. The math would work.