I hate the idea of a tournament, it's good on paper but it almost always fails on execution, just too many matches on a card and it drains the life out of the audience.
As of now I'm going with Orton winning this one. If they just do a regular 1 on 1 match then there is a lot of ways to get that title on Orton without Bryan getting pinned. You could do something along the lines of Bryan has Orton beat when Big Show comes out and decks Orton, leading him to win by DQ with the title in place. Also when its an Iron Man match its also easy to get the title on Orton with Bryan clearly being the better man. There are many ways to go about this but ultimately I think its clear cut that Orton is winning this one.
Right now I think HHH vs. Daniel Bryan will end up on Wrestlemania 30 (maybe even for the title) with Bryan finally getting his big win and ending the feud. It's a long ways away but as of now I'm gonna assume that this feud is going until Wrestlemania which is the right idea. Luckily with WM30 I think a ridiculously stacked card is in the books so this match will be one of the main events with maybe Taker vs. Cena or Taker vs. Lesnar closing the show (fingers crossed). Bryan will get a big match at WM30 no question but by that time it won't be Orton (at least I don't think so). To get to Triple H though he's gonna have to beat Orton first but Battleground is a little too soon for his time with Orton to be over and if he beats Orton there you gotta kill 6 months between the big Triple H/Bryan match.
All in all I'm going with Orton beating Bryan by shady circumstances to win the title and he will hold onto it probably until the Rumble when Bryan finally wins the title and finishes him off for good.
Make Dimension X great again!