Re: If Vince Russo was booker, and this was 14 years ago...
People often forget that the guy did have his moments of genius. It'd really depend on which Russo you'd get though.
Good Russo would have an interesting scenario similar to the one OP explained.
Bad Russo would make CM Punk Vince McMahons biological son, have 2 of the divas in some sort of pregnancy storyline, have a who murdered [insert wrestler here] storyline, make Cena beat Undertakers streak and something like making a retired Booker T the WWE Champion