Wouldn't it have made more sense for GAB '88 to be headlined by Flair vs Sting since Sting had a claim as having been the guy to take Flair to the limit, and a grudge match between Luger and Windham since Luger had been turned on by Windham (no homo). The booking just seems a bit weird. Luger gets turned on by another guy (no homo), but wants to fight Flair instead. Sting is all okay about not getting the title shot even though again he had just taken Flair to the limit a few months prior. If Luger vs Flair had been the plan wouldn't it have maybe made more sense as the guy to go broadway with Flair and Sting and Windham as a team instead?
Anyway, yes, the logical progression would have been for Luger to go through Windham first and build up to Flair at Starrcade, but I think your'e underestimating how deeply in debt up to his damn eyeballs that Jim Crockett really was. He needed that sweet PPV cheddar NOW and Luger was the guy he had the best shot with. I mean, obviously with hindsight we know that was done after Starrcade 87 anyway, but in his mind Sting v. Flair wasn't drawing a buyrate yet and survival was his only motivation.