I think the benefit for Jay going to AEW is that he's already introduced so the transition wouldn't be as hard to make. Something AEW has right is at least acknowledging and building off of wrestler's history outside of the company. If it wasn't for the news of Vince being back, I'd have more faith with Jay in WWE because he is good and assuming Roman drops the titles eventually, he can rise to a top level heel.
AEW still has issues around a somewhat bloated roster, a need to rotate talent a bit better, and maybe a few things, but I think he'd probably be an instant player near the top of the card like when Danielson and Cole signed.