I really hesitate to resign Donaldson when the goal to try and setup the team for a constand run of contention in the future, and you've got 2 potential blue chippers coming along within 2 seasons, and adding potentially 2 more to that as a trade return from a Donaldson move just makes all kinds of sense. Multiple young guys who come up together as stars and basically take over the team, ala the Cubs.
His value is at it's peak, is only going to go down unless he's the next Beltre, and if he's signed he will represent 1 of 3 mid 30s players with monster deals on the team, which is exactly what doomed every other team like that in recent memory before they fell off the rails and ended up having to go through multi-year bottom dwelling suckage, with the exception of Boston and NY who had the foresight to get out before the crash, but they also have financial freedoms the Jays don't have (rightly or wrongly, thats just how it is).
Thing is... I also get the argument to retain him... he's a frigging beast when he's on the field and the fact that he's there helps Rogers sell the team to all the casuals, which is who they need to convince to watch them on TV and buy tickets.
It's a delicate balancing act that Shatkins has to navigate this upcoming offseason.