Hernandez, Chapman, and Gurriel are all FA's after 2023, and I can't think of one prospect today who looks like he might be ready to take one of those spots by 2024. Maybe Orelvis if his 2023 looks better than 2022 but expecting him to hit the ground running if he does make it is probably going to end in disappointment, and the Jays can't afford to spend the last two years of Vlad/Bo's control (2024-25) with a 3B who may need a few years to develop. I don't see any OF's on the horizon unless I'm forgetting someone. The Jays really need a CF but that's the toughest OF position to fill. That's not even factoring the more obvious holes, which are bullpen (clearly), and the rotation which will not have Stripling and Ryu next season, and we have no idea what is happening to Berrios. Kikuchi also sucks right now, so that's an issue.
It's going to be very interesting to see what they do this winter. If they are seeing the same thing I'm seeing as far as the overall state of the roster/farm system, then I think they do some riskier things this winter to maximize 2023-25 wins. By riskier, I mean "sign Edwin Diaz to an insane contract" type of risky. Of course, if the Jays go on a magical run this October, then obviously that changes things.