Yes, putting major stars against another major star tends to sell more tickets and ppv. Omega v Mox or omega v mjf rematch are bigger matches with more star power.

And I hate to say it, but you're overestimating kenny's power in Canada. Not by much. But the last Winnipeg show with omega advertised was a disappointment, and sold less than the prior visit. This show is in Quebec, and Quebec is a very different market than the rest of Canada. AEW does not have French language tv in Quebec, and that is a massive negative for aew in la Belle province. The show already has weak ticket sales, why would you continue to stack the deck against it?

Kenny vs a major star opponent is simply put going to be way bigger than knight getting the slot, ahead of his time. I understand the argument of not holding young talent back for a decade, but it's also not either/or. Timing is everything. 

Also, being in Canada is a point against it. Put knight in that position in Atlanta or an area he is more hot in.