I think JvR gets closer to $6 million AAV on his next contract. His next contract is probably going to be his last opportunity to really cash in.

A couple of my thoughts: Dermot and Valiev hopefully make the team before Marincin stays. Hope than another centre such as Brooks or even a UFA is on the team before Ben Smith. Would like to see Nylander develop as a centre and have Bozak gone (although I have appreciated Bozak throughout the years). Maybe Kapanan and Marner develop as top 2 RWers. Brown and Hyman as 3/4 RWers.
LW seems confusing.....I doubt if the Leafs sign JVR to big time contract. Same with Komarov....maybe a replacement ready in 2018. Leipsic I don't think he's an NHLer.
LW maybe Lindholm and Grunnerstrom? fill two positions. Do Johnson or Tishakov? fill two. Still as you suggest on your post...looks of cap to fill a position or two.

I can already see the bad publicity over the "KKK Line" lol

id prefer to go longer term with Nylander and give him a bit more money. And i think you have him a bit devalued here. Its seems the going rate for a RFA scoring winger is around 6 mil, where i think he should be.

Call it the "Trump Line"

JVR is a similar LW to Ladd and He only got 5.5 per year so what makes JVR worth more than Ladd? Also, if ge wanted to stay in Toronto and finish this he will need to leave money on the table. Marincin, Smith, and Lepsic are Depth forwards on this roster which prospects do you wish to stunt to put in the press box? Nylander is a talented player but if we can keep Bozak who all do respect to Nylander is a better 2way player than Nylander that gives us more versitity in the roster. Also, I am hopeful Nylander leaves money on the table when he signs seeing if he wishes to play with Matthews, and Marner and compete for cups all players will need to just like Kadri, and Reilly did this past offseason. I do have concerns about our LW situation seeing though skilled we seem to lack players that can create space for themselves and their teammates and JVR at around 5 and Komarov at 3.5 will allow us to minimize free agent signings that always seem to cost more.