He probably would've turned into a babyface again in a feud with Kurt Angle
I can also agree with this
I think had he stayed he would've ridden out the Attitude Era as a heel but say around 2001 and after he would've turned back face especially if later characters like Angle, Guerrero, and Y2J are heels.
Some good scenarios in here but I strongly disagree with the upper midcarder. This is Bret Hart. He would not have been top top dog forever but he would have stayed in the main event scene.
I didn't mean upper midcarder as an insult but in terms of priority he'd be 4th at best behind Austin, Rock, and HHH. I look at him in the Attitude era as the guy who could mix it up with the Taka Michinokus and Tajiris as well as the Austins and Rocks and no one would bat an eye.