I have to wonder if Owen Sound and Kitchener made a mistake in going for it last season instead of this season. Much of their cores are back, but they made expensive additions last year and can't afford it now.
The path to the finals would have been far, far easier this season. There isn't a dominant team in the Conference with a shallow Knights team and a rookie-laden Hounds roster battling for first.
I believe the Rangers decision to go for it last year was made at the time they made the Jeremy Bracco trade to Windsor. Because it was probably at that time that it was determined that Logan Stanley would come to Kitchener in the off-season to complete that trade. No way they have a graduating Logan Stanley come here without trying to go for it.
Maybe they did not have intents on going for it last year before that trade, but since Bracco would only go to Windsor, and Windsor's lack of young assets and picks at the time, may have made Kitchener management decide, "Let's make the most of a bad thing" (Bracco's refusal to go anywhere but Windsor), take Logan Stanley, and then put in motion the building process for a long run last year.
The Rangers had the assets to do so. It also could have been as far back as the Bracco trade where preliminary talks started concerning the Logan Brown to Kitchener trade. There were rumours out there last year that Brown to Kitchener was a done deal long before it happened - likely because Ladd couldn't be involved in the deal until the January window.
Some even opined that Windsor may have had some influence on who the Rangers would select with their 2017 1st round pick since it was already determined that player would wind up in a Spit uniform.
Of course, we'll never really know if that were true.