This leaves us worse off

And how’s that? You shed a ton of cap space and gain 4 useful pieces + room for a goal tender. Tavares is good but he is dead weight in the playoffs. I’d prefer not to take him, but taking him gives the Leafs room and balance

this cripples us in about two years

Not saying I agree with the proposal. But, how do you figure it "cripples" you? This would give TOR a ton of cap relief through the next bunch of years without really effecting their skill level, TOR has plenty of quality prospects in the pipeline to fill holes and possibly progress into bigger roles, there are tons of promising players that could be had in free agency through the next few years too. This concept would solve a lot of cap issues and get rid of a lot of dead weight for TOR.

Gets rid of about half of our future and then towes walks from the leafs, we have no cap to resign the other guys and keep Matthews either then we are just stuck in mediocrity