I'll co-sign on both the main points (Vince's hand was forced with Austin, and Attitude era WWF was pretty jank).
WWF/E got a reputation for building up talent while WCW catered to the older stars, but a big part of that was just necessity. With Michaels retiring, it was either let some new guys carry the company or what, bring back Yokozuna and Bob Backlund? Competition from WCW was important, not cause it made the WWF try harder, but that it literally took away the other options. By 1998 WWF had one former title holder active (Undertaker) vs. at least five former WWF champs in WCW (Hogan, Flair, Savage, Nash, and Hart).
As for WWE TV in 1998, it was mostly awful. It got super popular, but he's right: go skim a few CRZ recaps. It's not pretty.
One thing I haven't seen people talk about (though I basically just read the threads here and the articles at Grantland) is the preference for WWE guys. That is, wrestlers who only got exposure in WWE, and were maybe even trained by the company. Around 2002 you started seeing guys who came through the WWE development system: Cena, Orton, Batista, Lesnar, etc. I haven't followed the last decade, so I don't know how long Tough Enough went on for or how those kids fared. But the WWE brass certainly seemed to be more dedicated to homegrown talent (or company men if you prefer) over guys who made it big on the indy scene, or WCW transplants.
It's understandable that they'd prefer to deal with people whose wrestling careers are basically symbiotic with the company rather than someone who's created their own brand, either outside the company or as an undercard performer with a groundswell of support. Especially after going through the talent exodus to WCW. But it's another thing that could work against Bryan.