I was having Austin fatigue in late '99 but coming back after a year off revitalized him for me. I can't imagine a scenario where popularity doesn't drop in 2001 but there were still fresh opponents for a face champion Stone Cold. Angle, heel Jericho, DDP, Booker. "Goldberg." No I already explained
why that couldn't happen. RVD, but the crowd would have turned him face no matter what. I think they (Austin himself and WWF management) looked at Hogan in '96 and thought "yeah, the top face turning heel, that's what draws." Not when the fans actually like him!
And yes, heel Austin was entertaining. Long before we got two hours of irony and meme wrestling every Wednesday it was kinda funny to see the badass Stone Cold suddenly playing guitar, singing "Margaritaville" and getting beat up by his wife with a cookie sheet, but...that stuff actually sucked? And everyone knew at the time how lame and stupid it was? And maybe in 2000 we wouldn't get such a comedic portrayal since it wasn't until Steph took over creative that every segment had to have laboriously scripted comedy. But if it wasn't the time in 2001, it sure wasn't a year earlier.