The outcome of this match is 50/50 really, it depends on when Triple H is going to turn heel. If he is going to remain face for this match where they both respect eachother then Jeff should and will win IMO. If the plan is to turn him heel at Armageddon then Triple H will cheat his way to victory making Jeff look good in the process, thus not burying him and making it the perfect setup(Trips pushes Hardy while at the same time getting himself back in the title picture). Right now it looks like WWE is going to proceed with the latter since that is what the rumours are as of this moment.
Personally, I first thought Hardy was going to win this one, but now I think Triple H will get the win via low blow and Pedigree to become heel, but letting Hardy dominate near the end of the match even though he will be selling injuries from the ladder match with Carlito. This way, everybody will be satisfied, Jeff will look like he was screwed and betrayed by HHH(not buried!) and Triple H will begin his Road to WrestleMania with a storyline against either Orton, HBK, Batista, Y2J, etc. The more I think about it, this is actually the best move WWE can do, putting Jeff against Orton at the Royal Rumble is a waste(everybody knows Orton would win anyway), Jeff is the perfect underdog to participate in the Rumble this year where he will get a low number of entry and will make it to the final four, but not win(similar to Mysterio in 2006). This will keep the fans on the end of their seats thinking Jeff might pull it off and win the biggest match of his career, this is something the WWE will do in a heartbeat, no doubt about it.
As for the heel vs heel title match, I wouldn't be surprised if WWE will make it a Triple Threat match and add a face in there: Y2J vs HHH vs Orton seems like the biggest possibility.