Long-time reader who has been following wrestling since the late 1980s, but some things puzzle me:
1)  You say that the Austin heel turn at WM 17 was a big mistake. In the long term, you seem to be correct. However, at the time it seemed to make sense because Austin had pretty much run through the established main eventers (except Angle) as a face. Austin v. UT, Austin v. HHH, Austin v. Rock, and Austin v. Kane – all been there done that. Wasn't the concept at the time shake things up (by doing some of the same matches but with the face v. heel role switched) not a bad idea, at leas theoretically?

The heel turn wasn't a bad idea in of itself, the problem was that they pulled the trigger at the biggest show of the year, in Austin's home turf.  And he had no followup promo where he explained his motivation and made everyone hate him for it, leaving the whole thing kind of murky.  And then we lost HHH to injury soon after, leaving Austin as the guy who had to carry the entire heel side with that act.  

2)  I recall watching alot of NWA / WCW in the late 80s and early 90s and was a huge Sting fan.  However, everyone pans his first run with the title in 1990-1991.  I see that run not succeeding due to poor booking (see Anderson, Ole) and long-term, structural problems at the NWA (see Flair, Ric). Yes, Flair could wrestle but he could not sell tickets north of the Mason-Dixon line or west of the Mississippi. From 1981 to 1994 (up to Hogan taking the belt) and excepting the time Flair was in WWF in 1991-1992, he held the world title like 90% of the time.  During that period, some challenger would be given the title after a Flair loss but the new champ would have the belt a short period of time and be given crappy challengers (like the Black Scorpion) or Flair would be given a ton of rematches. Kerry Von Erich, Dusty Rhodes, Steamboat, and Garvin all fell into this trap. Why should have fans cared when they knew Flair was getting the belt back almost immediately and no other serious challengers were created to face the new champions? It seems to me that the promotion was set up to glorify Flair and Flair alone, even though his box office potential was limited.
Your thoughts? 

Well the system used to work differently, because WCW was a part of the NWA and you couldn't just switch the title on a whim.  You had to get NWA approval and work out belt deposits and dates and stuff, so generally guys weren't going to get long title reigns outside of Flair because promoters had no interest in a drugged up Kerry touring with the belt to their territory.  Plus let's face it, Flair was really good at taking care of Flair.  If it makes you feel better, they really did want to make Sting into The Guy in 1990 on a permanent basis.  But yes, you have nailed down a major problem that brought about the end of Crockett and many other promotions — same guys on top, no new challengers that fan buy into.