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Aside from the things pointed out above (in-your-face overexposure being chief among them) I mentioned before that he's a mediocre* talent who made the utmost out of every opportunity he was given. He had a money look, competent and well-rounded in the ring enough to work with just about anybody, and could promo... but there were always guys around hime who could do any of those things better than him at any given time. Not saying he is where he is SOLELY because he pal'd around with Shawn, sleeps with Steph, and was backed by the machine because of nepotism, but it had a huge impact on his career.
If he went a different way- that is to say, if he drew a different lot of friends breaking in and coming up- he would have been one of those "looks the shit", by-the-numbers prototypical wrestler that WWE would have looked at and thought he could simply get over on looks alone, and then when he didn't, they write him off as a lost cause and release him, where he would have returned to WCW and bounced up and down the card on the whim of whoever was in charge of the company that month. At best, unless he lucked into something that would have been his "Austin 3:16" moment, he would have been a decent upper midcard talent being pushed and depushed on a whim. His injuries would have had him slide farther down the totem pole.
With that being said, however, one thing that is CONSTANTLY said about him is that he's "a student of the game" and "has a great mind for the business", etc., etc. He strikes me as one of those guys who, even though he was realistically not the megastar he's made out to be, he knows his shit behind the scenes. Maybe he's like one of those career 2nd string QBs who goes on to become a winning head coach. Maybe he's applying that to being COO (the actual positon, not the TV kayfabe).
*WWE wise, I mean. Isn't really a bad thing to be so-so in the major leagues.
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