I've always thought Jim Crockett waited too long before putting Starrcade on PPV. If he puts the 1986 show on PPV, in a pre-WrestleMania III world, I think things go a little better for him.
Waiting until after WrestleMania III was a huge mistake, in my opinion
It wasn't really his decision at that point, as the opportunity to even be on PPV didn't come up until later in 87 once the relationship with Turner had been cultivated more and they had cable company support. If companies could just decide “Yup, we're going to do a PPV!” then, for example, ECW would have started them ages before they did. Plus Vince would have likely crushed him even more ruthlessly at that point.