When should Vince have stepped down

Knowing all that we know, when should Vince have stepped away from creative and given someone else the reigns?  Also when do you think the Mr. McMahon character jumped the shark and should have been retired as well, maybe after the DX Feud or earlier after
the Hogan match at 19?

I'd say that yeah, once Vince was fighting the one-legged guy, it was time to retire the character.