Thing

I mean it's not terrible. That's probably the best return you will get for Nylander so I would be fine with it. Nylander does hold more trade value then Severson so I think it does take that first for the leafs to move him. I would also be fine with the Carolina trade and Nashville trade as well. I think you could get at least a 2nd for Dermott tbh.

The only think I would question here is why Tyler Pittlick is in the top 6 and making over 2 million dollars. He is a 4th line forward and shouldn't be over 1 million. Also that 4th line is making way too much and Robertson needs to at least be on the 3rd line or he wont succeed.

My suggestions:
1. Remove Bogosian, Maroon, Pittlick, Thorton, Rodrigues, Bogosian and trade Engvall. We don't need Bogosian when Sandin is ready and Lehtonen can play the left side so that is just a waste of cap space imo and the rest of those players can be replaced with league minimum contracts. Removing all those players gives you an extra 9.45 million in cap space.

2. Have a 4th line of "?-Brooks-Spezza" with Spezza and the ? at close league minimum (or at least under 1 million).

2. With the new cap space, use the Vancouver pick and some other assets (perhaps Liljgren) to trade for a top 6 forward or sign someone like Hoffman and Dadanov in agency as you will have the space to do so. I would also move on from Kerfoot imo and try to find a cheaper 3C. Perhaps maybe if you throw some more stuff into the New Jersey trade they could throw in Zacha for example.

Robertson should be a middle 6, but since next season is his rookie campaign I wanted to shelter him a bit, have him focus on learning his defensive responsibilities, and learn from 2 on-ice coaches and potential HoF candidates.
Kerfoot deserves another kick at the can before he gets shipped out. Bogosian could be swapped out for a different veteran 3rd pair guy, but I think it's important to have that presence. Even if Sandin and Lehtonen are solid enough, I wouldn't want to rely on them without some kind of safety valve that isn't Marincin. Pitlick and Maroon might not be the exact players TO needs, but it's the exact type of players they need. Swap Barabanov and Pitlick if you want, I just tried to space him and Maroon out in the line-up.