No, I think he's allowed to request a trade at the end of the season (someone correct me if I'm wrong). If that's the case, then trade him in the offseason.
Not necessarily. In Toronto, he would know he was part of a team that tried to trade him. He would know his team was no better than third best in the division with no hope for postseason play.he'd be just as miserable a lame duck in Cincy as in Toronto.
In Cincinnati, he would have a team that wanted him and a winnable division.