Scott,
Before real-life events changed everything, what was the first point you realistically thought Chris Benoit could have become World Champion in a promotion? He was of course an internet darling for years before he got any kind of legitimate push, but before his Wrestlemania XX win, do you think there was an earlier time he could have won the big one? The 2000 feud with The Rock seemed like a candidate to me. His return from injury in 2002 could have led to a HHH-Benoit World Title match at WM19 (in lieu of the HHH-Booker mess).
He should have won the title from Steve Austin in 2001, although subsequent injuries would have made that a disastrous choice on WWE’s part. But still, they did the RAW and Smackdown tapings in Calgary/Edmonton with Benoit v. Austin on top both times, and he was at the point where he could have carried the belt for at least a couple of months. By 2004, they were clearly moving onto the next wave of guys (Cena, Orton, etc) and there wasn’t going to be any wiggle room at the top for anyone other than someone to make younger guys into stars.