Aside from the Vlad connection, I think the odds of Bo staying in Toronto are higher now mainly because I don't see his market being that big. All the big market teams except the Dodgers are set at SS, and the Dodgers don't seem like the type of team that would value Bo at $250-300M. You would think if they were going to give a SS that type of money then it would have been Seager. On top of that, there is talk now of the owners insisting on a salary cap, which means a guaranteed lockout after 2026 and who knows what for 2027, so I don't think too many teams are going to be spending absurd amounts of money for FA's other than Tucker and the top of the SP market (Gallen, Cease, etc). Bo's kinda in the middle range of being a very good player but not a superstar. In a market where teams are spending big, he likely would have made out well, but I'm not sure this coming winter will be that type of market.
The Jays will have the need at SS, they will have the desire to contend, and they obviously have the financial resources to give Bo what he wants, especially if Ed Rogers is involved and gets into the fetal position as soon as he meets with Bo and his agent like he did for Vlad. The caveat being if the Jays are sellers in July and move Bo mid season, but even then the Jays could easily just get under the lux tax and sign Bo as a FA even under those circumstances. I guess it depends on how badly Rogers wants to keep him.