If they actually run Bryan/HHH, I'd say the chances of Bryan going over are pretty good. There's always a chance they'll do one of their everyone-expects-this-guy-to-win-so-he's-losing swerves, though.
I don't think they run Bryan-HHH, though (or Punk-Trips, for that matter). Either someone politics backstage, or they simply decide they don't have enough faith in Bryan to give him that slot on the card.
Honestly, I expected them to start the Wrestlemania feuds by now. Royal Rumble-Wrestlemania is usually the one time of year creative can be counted on to come up with some compelling long-term booking.