Let's get crazy hypothetical here. You're reviewing the Raws leading up to WM 12. While we know Big Kev leaves for WCW, he DOES get a ppv main event in April (the awesome Mad Dog's leg match). If Mick was already debuting in promos before WM 12, AND shows up the Raw after to attack Undertaker, then why not have Mick debut at Mania itself. What better way to introduce a new character and feud then on the biggest show of the year. Nash and Taker could brawl, and Mick comes out attacks Taker and Nash wins. Nash uses his win to go for Shawn, Taker and Mick have insta-feud. It's weird to think of a world without the streak, but I always wondered why Nash (in storyline) would deserve a title shot after jobbing at Mania.
Bonus Question: Where else might you have pegged Taker for a loss at WrestleMania before the last few years? The obvious ones were HHH at 17 which we know now was political, and Orton at 21 in a "legend killing" moment? Are there any other actual times Taker could've/should've lost?
Really, there was little reason for Nash to be jobbing at that point aside from imminent departure. Turning him had really freshened up the character and they could have pushed him again with no problem. I like the cut of your fantasy booking jib with that one.
As for the second question, I think without question Flair should have won given the ridiculously one-sided beating that Taker delivered leading up to the match and during the match itself. He basically terrorized Flair's family, for fuck's sake! AA hitting that spinebuster and giving Flair the win would have exploded the Skydome, but of course it wasn't meant to be.