I was just watching Raw through 2001 and I really liked the build to Rock/Austin at WM17. Most people shit on Debra's involvement but I thought it did a good job of taking away a lot of cool factor to Austin in some ways. Here's this badass beer drinker who kicks ass. Then they have him "feelings". Then the teasing if his heel turn through the obvious(I need to beat you Rock) and Austin sitting back and drinking beer while Rock was being beat up. Also Rock was constantly booked in handicap matches during this time while Austin didn't wrestle or had more fair matches. I thought it did a good job of planting seeds so you could look back and say "well that makes sense".
The night after sucked though with Austin's whole I don't owe you anything deal and Triple H and Austin teaming up despite trying to kill each other(literally) a few months prior.
My question is: What would you have done with Austin immediately following his heel turn? Who does he feud with since Rock leaves? (I ask this because I'm fairly sure you aren't gonna say Undertaker and Kane.
I thought the direction they went with was fine, with Austin & HHH feuding against the Benoit/Jericho/Angle tandem, but of course that got jettisoned due to Benoit's neck injury and their total lack of faith in Jericho. But it was really giving them the rub and they probably should have stuck with it. And really, building to a big Austin v. HHH blowoff at Wrestlemania was a totally fine idea as well, but then you run into the issues with having the Invasion hanging over their heads, and Vince was trying to run with a million different "big ideas" at once like invading Alliances and trying to single-handedly avenge 9/11 through the power of Stephanie's promo, and it just turned into a huge mess by the end of the year.