In October, Ill be cheering for them to win. The IDEAL scenario is having several young guys break out, and the Leafs not needing a high pick to put together a good core, because a good core would already be coming together. Best case scenario is Rielly breaks out as the new young Doughty/Pietrangelo/etc, Nylander contends for the Calder, Kadri progresses into a ~60-65 point two-way centre, Gardiner rounds out his game and breaks out with a 40+ point season, and our goaltending bounces back to above average.
In saying that, the above is very very unlikely. Regardless of where the Leafs finish, I want to see some core players moved out, a focus on drafting, and a focus on asset management. We need to beef up the farm, and continue getting value for guys instead of losing them for nothing. Which means very likely another bottom 5-10 finish next season, unless our youth surprises (as opposed to our mediocre lazy older core surprising, because theyll have mostly been traded away). I also dont want to rush guys, and would lean towards Nylander getting a full season as the Marlies #1 centre, that way he can get his first full season as a centre in the last 2-3 years.
I also dont want to see the offseason defined by moves that prioritize making the playoffs next season, but instead on putting a solid foundation in place longterm. Remember, all top 3 picks go to lottery next year, so even if we finish around ~20th (previous "no-mans land"), we'd have a shot at three different lotteries. Sell off pending UFAs and some of our old core on top of that, and even if we dont end up with a top 2-3 pick, we should still be adding substantially to the farm, which will improve our odds of hitting a homerun simply via volume of prospects.