He was right to tell Hogan "nah I'm good" when Hogan contacted him to let him know WCW was looking to sign him and offered Vince a chance to top their offer. Not because it helped WWF financially or star power wise, but because he was fully on board by that point with the idea of creating a new generation even if it meant losing his biggest star of all time.
He was right to admit to the roster that he had been a bit behind the times around the mid-90s, and encouraged them to throw their own creative ideas at him and tweak their own characters.
He was right in most of the instances he used celebrities to bring attention to the product, especially the build to the first-ever WrestleMania... including the decision to not only incorporate the music of the time into his TV shows, but to do specials on MTV (which was the biggest thing going at that time), the NBC deal, the cartoon, toys, etc.
He was right about Cena in hindsight. They definitely went overboard at times and had him as the longest-running top guy since Hogan, but I don't think he had another star during those years that could've been as kid-friendly or mainstream, had very little injuries, AND avoided trouble in or out of the company (imagine if for example, he had picked Orton, Edge, or Jeff Hardy instead).