I agree, with Robertson and Sandin set to graduate and back to back seasons without a 1st its time to recoup some future assets or ELC NHL ready players who can fill depth roles.
Ideally you deal Marner for a haul, but there are few teams who can take on his cap. Realistically were looking at Nylander + Johnsson + Kapanen + Andersen in separate deals for futures to cover the cap of AP. The problem would then be filling out the remainder of the roster.
If AP is the target, both Marner and Willie will be gone. As I don’t think any teams have the cap space and prospects + picks to just take on any one of them without sending players with salaries back. Assuming the other two teams trading for them have what the Leafs want say a Dman and a forward with half of MM and Willie cap, Leafs would free up a bit under 9mil cap space, which might just be enough to cover Pietra’s cap hit.
Trading all Kerfoot, AJ and Kap to sign AP won’t work as that will only free up 7mil due to getting replacements.
Any combination of Willie plus one of those three won’t work due to Leafs needing to find replacements plus the player coming back via the Willie trade.
Any combinations of Marner plus one of those three will might work depending on salaries coming back.
Ideally, trade both Marner and Willie to get players plus cap space to sign AP, but that will be very complicated even for an experience GM like Bowman or Lou. Just too many moving parts.