I think this original question is a hard one to answer without knowing what happens with the Celtics over that same stretch.
For example, if Gordon Hayward returns to 85%-90% of the guy he was before we signed him, then there's a good chance Boston could probably move Hayward's contract to clear cap space.
But assuming Hayward has returned to that form, you probably don't WANT to trade him unless either Tatum or Brown (or both) has made a major step forward, because if they haven't then Hayward may be too important to move.
So it really depends on a lot of things.