It's what makes sports great. The added pressure of performing at the top level in a short timespan. The best regular season team doesn't always (in fact, rarely) wins it all, and that's great for any sport. There's a human element that can't be quantified. There are market pressures that can't be quantified. I certainly get all of that. It's why we watch the games.
As fans, only thing you can hope for is having the ownership and front office that tries to capitalize on as many market inefficiencies as possible to maximize the controllable aspect of winning championships. My point in previous posts is that on paper, Toronto has done a better job of this than the Islanders have leading to more regular season success. I still believe context matters. The Canadiens made a run in the bubble. They made the Finals. There isn't a person on this planet that thinks they've had more success than the leafs. They rode their goaltending and stars aligned in other ways.
My original point however, is that, the Leafs, have acknowledged there was an issue and every year made some moves to adjust even though they are to the cap. Every year, they have gotten better and made adjustments. The Isles and Lou on the other hand, walked away from their last playoff run thinking there wasn't anything to change. Anybody who watched the playoffs that season, cannot and should not have agreed. Long road trip and COVID aside, that team was not making noise in the playoffs. We know this because that was the same exact team they iced this season, where there have been no long road trips and COVID. Lou's process has been defective because he got fooled by the playoff runs thinking they were close as constructed without tangibly improving (No, Romanov doesn't count, not yet anyway).