Ric Flair's book went into considerable detail about the end of The Jim Crockett era. Some things to consider...
The NWA programming and brand was outdrawing WWE in much of the core areas (NC, SC, GA, Kentucky, Missouri) and thanks to TBS exposure was doing drawing ratings and crowds farther out into WWE areas in PA, etc.
Flair pointed out that when Vince entered a region previosuly dominated by another company, he moved in slowly, staurating local TV with his programming, then appearing only a few times, as if each card was a "Special Event". They drew well because of it but WWE still concentrated the bulk of their touring business in their core areas. They ran Madison Square Garden almost every month but only made ocassional trips to St Louis.
Crockett in contrast, in an effort to outgun Vince, wanted to run every 4-6 weeks in these other towns, traveling way out to the west coast, etc every month, the appearances became more routine and less special (making it harder to consistently sell out) and the travel expenses were huge.
Vince was forcing arenas to sign "Exclusivity" agreements, stating that they would not run wrestling shows except for WWE. Crockett made no such argreements. He could have negotiated agreements likley in his backyard (Carolinas, GA, Kentucky, Tenn, maybe even St Louis) where his brand was more establshed and an easier sell. In Philadelphia the NWA was huge but they couldnt get into the top arena. Same thing in Chicago. Vince couldnt stop them from running cards in his cities but he could stop them from drawing huge gates by keeping them in secondary arenas. I know in Pgh it took a few years before our Civic Arena was willing to negotiate that kind of deal with WWE, somehow despite Pgh being a core WWE city they let the NWA into the Arena. Their first card in 1985 drew horrible but then they topped 16,000 in Oct 86, 17,000 in Fen 87, 11,000 in July 87, 10,000 in Sept 87, and drew well (at least when Flair appeared) through 1989. Vince would have been slowed down if he had been relegated to secondary arenas when he tried to play in the Mid South region and Crockett would have saved a boat load of money had he not toured nationwide every month, instead focussing the house show business on his strongest areas and only occassionally running "SuperShows" in other regions, ala Vince.
When Crockett bought The UWF, he wanted both the talent and their existing TV contracts (they would have been voided if UWF went under and possibly sold to Vince). However, the company was well into massive debt and many of those TV deals were under water (the UWF owed money). Essentially, not only did Crockett spend a lot of cash to buy the failing company but he then inherited all their debt. Contrast that to Vince when he purchased WCW, he paid for the rights to their footage but would not take any takent contracts, instead negotiating new deals with buyouts for talent he was interested in. Hedid not buy any physical assetts of the company (offices, property, etc) so he took on no leases, debt etc. He got the most valuable assett that they had (archived footage, worth millions in repackaged DVD's plus useful in promoting any talent he did sign) without taking on leases, bank loans, property mgt, or talent contracts. Crockett way over extended himself. He could have cherry picked the TV deals in areas he wanted, and could have negotiated new deals with talent rather than take on the entire roster, much of which wasnt useful to him but he was obligated to pay. Had he struck a deal like that, similar to Vince's WCW buyout, he would have saved money initially, avoided the massive debt issues, and only been on the hook paying that talent he really wanted (Michael Hayes, Steve Williams, Sting).
Crockett also relied too heavily on Dusty Rhodes for booking. By the middle of 1988 things were getting stale with every major angle designed to somehow make Dusty rise from the proverbial ashes and trump The Horsemen while The Horsemen essentially always trumped everyone else leading to their ineveitable showdown with Dusty. There were times, particularly in 1985 (Starrcade), 1986 (The Flair takes on the whole roster in a month storyline that sees him go undefeated until his next to last match against Rhodes), as well some anciliary storylines involving Rhodes & Tully Blanchard (1985 Great Am Bash & The 1987 $100,000 Challenge come to mind) that were very entertaining but you can only do the same thing so many times before it gets old. Dusty was very creative but too centered on himself, given his age he should have been pushing Sting & Luger and maybe Whyndam more as top faces to oppose Flair, rather than basically feeding them to Flair until t was time for their next go around. Dusty could have done what Flair & HBK did in WWE during the last runs, have their share of moments as prominently featured major players but also take a step back and help elevate others (Orton, Batista, Edge, Cena). Neither of them was humilaited or forced to endlessly job, each winning their fair share of matches but they didnt dominate the programming constantly. If Dusty had taken a role like that by the end of 86 the booking would have been much more consistent across the board and likely better