PLD still has full control of what will happen.
Since he has yet to sign a long term contract, any team that will be interested will be very careful. That can be a major turnoff for any team willing to offer something serious, because he could decide to just sign for a year and be UFA afterwards. They will want some guaranties that he will sign long term, and he could just say that he would not sign with a specific team.
If Montreal really is his dream destination, he can easily make it happen.
I don't think money (higher taxes or higher salary) is really a decision factor here. He already earned 29.6M in his career, so an 8 or 9M contract for eight years will not really make any difference in his life. Whether you earned 93 or 102M at the end of your career, your life will pretty much be the same. So you may as well enjoy the next 8 years instead of going to a nightmare for a couple more millions.
So I guess we will see what he really wants to do, but honestly, I am not sure they should invest too much in such an attitude. You don't win with that kind of guys.