I think it (Taker/HBK 2 at WM) will happen and I don't see HBK winning. It makes no sense for Shawn to win because he doesn't have much to gain nor does he NEED to gain anything. He's already one of the greatest ever and ending The Streak would be a mention Michael Cole can throw in during every HBK match and nothing more. Retiring Ric Flair at WM is enough for Shawn.
I think the streak should end when Taker is going for 20-0 (assuming he sticks around that long) and it should go to a younger talent who Taker would be putting over in a huge way and in essence "passing the torch" to. If I'm not mistaken, Taker is currently at 17-0 so he'd be going for 20-0 in 2 years and who knows who will be in need of being put over THAT much (Sheamus immediately comes to mind but chances are he'll be way over by then - maybe ending the streak will take him from being over to being elite?) by then so we'll have to wait and see.
Another idea would be to keep Edge undefeated at WM (which he is, correct?) and maybe have a Streak vs Streak match at a WM after this year's. I would give that win to Edge because him extending his streak makes more sense since he'll presumably be around a lot longer than Taker will. Who knows, maybe this match will happen this year?
But if Taker/HBK 2 does take place this year, it can be made into another classic that goes back and forth for 30+ minutes until the Undertaker finally gets the win, again. This time, after the match, have the 2 men stare each other down with the Taker extending his hand out afterwards to acknowledge HBK's amazing efforts and then Shawn can shake his hand to finally admit defeat and move on. He'll (Shawn) probably be taking another extended vacation after WM anyway.
We shall see.
