I'm genuinely surprised by Toronto's lack of playoff success so far, for what it's worth.
It's hard to predict an actual cup win - but based on their teams over the past few years, I truly believed many times they were bound for playoff success in some way. I thought they might surprise and make the finals last year for example, with the East seeming a bit more wide open than usual.
I guess what I'm saying is, their fortunes have to change at some point. So I absolutely expect them to have a monster playoff run with this core in the next 2-3 years at least once. Does that mean a cup? I dunno - unlikely, but possible.