I feel like getting Manny and one of Sale/Cole/Bumgarner next offseason is better than getting both Machado and Harper now. The Sox need a legit ace to put at the front of an inexperienced rotation.
I've said it a billion times, but I still think Fulmer could be a solid reliever. If he can somewhat command his pitches, he should be good enough to pitch an inning at a time out of the bullpen.
Hector is really putting all his eggs into the Machado-to-the-White Sox basket. I find it hard to believe he would put his reputation at stake if he didn't think it was going to happen.
That would be ideal, but it's hard to envision a scenario in which Machado doesn't get the opportunity to bail out at some point if he so chooses. I would be ecstatic if they could do what you said though.