If you are trying to win a championship, you want the best players in the playoffs.
We can agree that Wakely is the best player. No doubt. But, if rumours are accurate, he wouldn’t go to Kingston. So, does Kingston then pivot to the best available RIGHT NOW and call it a day? Or, do they wait for the best to become available? If they can add a stop gap OA for peanuts, similar to what Ottawa did last eyar with Lawrence for an 8th round pick, then I am all for it. Jsut replace him at the deadline. But, if they have to pay two 2nds, and a 3rd for another player of the calibre of Guindon only to pass up on (insert whatever name you want here) at the deadline for an additional 4th round pick added to the package, then yes, I do believe it is more valuable to wait.
Additionally, it gives the Front an opportunity to uncover a hidden gem in their lineup they either didn’t know they had or didn’t think would step up this quick. That alone may alter the decision on which OA is most valuable.
I understand your point regarding who they play makes a difference but if you are shooting for a Championship, at some point you need to play the best teams. I’d rather play the best teams with the best possible lineup as opposed to getting an easier 1st round and head into the 2nd round with less bullets in my gun.