I can't disagree much with NightShift on Edge being the guy to surpass the legendary 16x mark. He does have a tendency to get the title lose it and get it back over and over so it would make sense that he would by accident surpass the 16x mark.
Between the given options though I'd have to say it's a toss up really. Negating everything going on at the moment, I'd say that Kurt Angel has a better shot of doing it in TNA than Triple H doing it first in WWE. Kurt Angle is a steeple in the World Title picture of TNA and it is only a matter of time until he gets the title again unless he leaves. It doesn't matter who is or is not the champ at any point, Kurt Angle can take it away from them and most likely will be back in that picture after this whole World Elite business is over.
Triple H on the other hand I think is the more deserving of the two, and should be the most likely. But take a look, I am a huge Triple H mark and I'm not afraid to say or show it.
Seriously though, this guy has earned it. People are very quick to judge Triple H and I understand why. He is an easy target since he has been in the title picture for going on a decade and his personal relationships haven't helped the argument of why. I say it's because he's the best at what he does, others say because he's married to the bosses daughter, sabotaged other peoples careers, and wormed his way onto the writing staff to do so on and on. Take a good look at his career and you'll see that he really has earned it. This guy payed his dues, took his bumps, and worked his way to the top, that's all there is to that. Some people have a problem with it because their favorite guy didn't and it's a damn travesty but that's the way the cookie crumbles. Some have to lose and some have to win. Triple H has put plenty of guys over no matter what your definition of that be, he's had to come back from injuries that would retire most people, he always gives his best in the ring, is arguably the best at what he does, and I'm sorry, but Ric Flair gave this guy the nod of approval already and set up for him to be the guy to surpass his record 16 world titles.
I think if it is going to be done with Triple H, sooner would be better than later because let's face it he's not getting any younger, and time could be running out at this point. I don't know how it should be done, but I do believe he should be the guy to do it. Kurt Angle, is a very credible candidate and I wouldn't be upset at seeing him do it either though. Time is a factor for him as well, no telling how long that neck will hold up.