Scott,
Recently listened to a Sid shoot interview he did with Hannibal, and what I found interesting is that he publicly refuted the notion that he asked to be turned heel during his first WWF run in 1991.
He states that not long after the injury, Vince came to him and stated that they were “changing directions” with his character, which upset him because he was basically lied to and the top babyface position was taken from him, costing him merchandising etc.
So if the arm injury does not happen, would Vince still have made the decision to turn him heel that early on in his run, with the massive crowd pops etc he was getting? Or does Sid blow off his feud with Jake Roberts and maybe get shot right into a feud with Flair for the world title?
I think it's hilarious that he would take Vince's word about being “top babyface” when HULK HOGAN was still alive and under contract in 1991.
I dunno, I think Sid v. Flair sounds like death if they tried to run that as an actual main event program around the horn. Realistically the spot for Sid was top heel.