I think Tavares, Copp, and Nylander would be a really good second line. But this team would struggle to make the playoffs, let alone make it past eastern conference rivals like: Tampa, Carolina, Florida, and even Boston in the first round

You cant really ask to not be roasted and put that arizona trade down. It's really really really bad. It makes no sense on any level for Toronto.

The major benefit is the cap relief while still remaining highly competitive. It starts a retool more than a full rebuild.

And you want TOR to pay their signing bonuses on top of that?

But you've traded the pieces you would want to tool around. Why retool around Nylander and Tavares?

I know this is a lot more radical than most fans want to go, but I don't think it would be a bad as you think.
I think Keller and Schmaltz are better than you think. They are not on the same level as AM and MM, but keep the team completive and allows them to retool in about 2 years.

Thats the only way AZ does it.

More about retooling around Keller, Schmaltz and Copp and then having the flexibility to change the rest.

ARZ wants the far superior players, and also wants TOR to pay their high signing bonuses on top of that? And TOR accepts this?

Only if they want to radically change the core and start retooling. Not sure what AM34 does in 2 years so this would allow them to start retooling if they think he will be gone.

I don't see Tavares or Muzzin waiving their NTC's and I don't think it is as easy to dump some of the other players like Mrazek and they won't get as much of a return as they think on Kerfoot and Nylander etc...