Here is how I see the Jays re-tool this winter going. (I'm not sure if I would go the re-tool route - I'd rather build a sustainable 90 win model, rather than a team that if things go well wins between 85-92 games, but not every year.
1. Starters - I assume the Jays are going to roll the dice with the current starting rotation / org depth, and invest all their FA resources into bats and the bullpen.
Gausman, Berrios, Bassitt, Francis, Rodriguez, Manoah, Tiedeman, Bloss + perhaps a 5th/6th starter type FA signing is what I suspect they will roll with, And it could work if all things work out well, or if one of Rodriguez, Manoah, Tiedemann take a nice step up from what they contributed this year.
2. Bullpen - I think they will try to acquire at least 3 quality relievers - to add to Romano, Green, Cabrera. They will not tender Swanson. At least 1 will come via FA, and at least one via trade. Relievers don't take the resources that a bit or starter does to trade for (especially in the offseason), so I can see them trading 1 or 2 of the following (Wagner, Loperfido, Jimenez, Steroid Boy, Horwitz, Barger). They may have a surplus of that B level prospect.
3. Bats
a) I think they bite the bullet and sign Guerrero to something start with a $3 (as in $300 million+)
b) They keep Bichette - they don't sign him long term nor trade him. His trade value is not that great anyway. He is on a very reasonable contract for 2025 ($12 million), so if he comes back plays well and they lose him so be it if they are in contention. Another way to look at is, how much trade value would you give up at the 2025 deadline to acquire a player like "good" Bichette. Now you don't have to give that up to get a pending FA at the 2025 deadline. It might be best just to keep him, then accept the compensatory pick when he leaves. Long term it might not make the best sense for the team, but for re-tool it is probably the best.
c) They go hard after Anthony Santander as the big target of their FA spending.
d) Whether they go after Santander or not, they try to get at least two very solid bats. The other bat might be targeted via a trade, They won't spend any money on starters, and they can trade prospects to get a cost controlled reliever.