I could see us making a significant trade or two, and a significant UFA signing. I'd be quite happy with moves along these lines:
* Kapanen + 2017 1st for Tanev
* Carrick + Rychel + 2018 2nd for Pysyk (there are rumours about this, who knows if true)
* Sign Oshie
* Expose Bozak in the expansion draft
Leivo - Matthews - Marner
JvR - Nylander - Oshie
Komarov - Kadri - Brown
Hyman - Boyle/Gauthier - Martin
Soshnikov
Rielly - Tanev
Gardiner - Zaitsev
Hunwick/Dermott - Pysyk
Andersen
McElhinney/UFA
This is what I think "going for it" would look like for the Leafs - giving up picks and non-super-core young players for some good fit types in return (like Tanev and Pysyk). I think the above team would be a pretty scary/competitive playoff team, if healthy. Going for big stars and giving up any of our big 3 doesn't make sense, but there are other young assets we can leverage if we want to improve quickly.
At the same time, I'd also be happy with largely staying put over the offseason, and just seeing how our young guys develop. We were already a playoff team last year, and our core is super young, we should improve significantly without any major moves. Our window is long with this core, and if the right deals aren't there, doing nothing is a fine backup plan.