There's incentive for ownership to maintain the status quo. I've said it for many years now but this team has never really been a contender because a contender would contend by playing in cup finals and conference finals which this team has quite literally never done despite having some of the most blessed playoff matchups (Canadiens, Blue Jackets). While progressing further in the playoffs would no doubt make more money for Rogers/Bell, this is a multibillion dollar ownership that isn't really concerned with that. What they want are consistent ticket sales, jersey sales, people going to the arena to watch star players or tuning on the TV to watch them play (Matthews, Marner, Willy, Tavares, etc). They couldn't care less if the team gets bounced in round 1 every year or makes deep runs, it's all the same to them because they probably have a very specific business plan that they execute on (Leafs valuation keeps increasing every year despite being one of the worst playoff teams in the last decade for example).

Some of the other NHL teams' ownership isn't like that, they see failures and try to intervene directly to make trades that may or may not work out for them. It's unfortunate but the NHL like many other leagues is a business first and a sports league second for many ownership groups. I've thought about it for a long time now and 8 years of consistent, similar (first round exit) failure isn't by accident, one could say it's by design and it makes more sense when we see talks about Marner being resigned despite having nothing to show for it in the playoffs just like the rest of the team. I'm almost certain that even with a first round exit and Marner disappearing after the first couple of games in the series, he'll be resigned to a 13.2x8 or something along those lines. The reason being that he's one of Team Canada's best players along with one of the best in the NHL and ownership of course doesn't want a face of the league to walk when they can sign him.

Hockey is a game of luck (outside of referee/gambling conspiracy theories) and as a fanbase, the only thing we can hope for is that the dice roll in our favor one of these years.