Toronto has moved to a place where they now ice the best lineup possible. They are no longer in development mode.
This.
The time is now. IMO, they are amongst the elite, or at the very least just a piece away from the elite teams (Stl/Chi/Bos/Pit/LA), and have surplus assets to trade to get there (defense and goal, perhaps). The top six has two pairings that give opposing defenders fits, in JVR-Kessel aka "van Kesseldyk" and then Lupul-Kadri aka "Kadruple". The supporting cast is very respectable in Clarkson, Bolland, Kulemin and Raymond. Frattin, Grabo and MacAurthur were also a great supporting cast, but they seemed to lack in grit and leadership. Defense is as deep as its been in years. Gone are the days of employing defensive question marks like Komisarek, Schenn and Kostka. Instead, we have better talent in Fraser, Gardiner and Reilly. And goaltending is as solid as ever, with Scrivens gone and Bernier in.
Put the talent out there, regardless of age, and squeeze that sponge dry. Go for gold.