I think your first point is the really interesting one - I can't see him kicking up a fuss, but he'll probably be quite firm behind the scenes saying it's time to move.
He's given great service and we've given him great development.
Playing hardball to keep him is probably more damaging than letting him go for a reasonable fee.
The perception of his injuries and it starting to become a pattern moves him out of the top bracket for a buying club I think.
Man C and Bayern are the only clubs I can making it work and will probably involve a moderate fee plus a couple of players.
Equally I wouldn't be surprised to see him stay, but I don't think this is a time where Levy would play hardball like Modric, Berba, Bale.