It will be a LONG time before Triple H retires, but, given if all 3 of these men would retire tomorrow, I agree with all that Triple H will stick around and take on some kind of role long after he is done in the ring. I can see him being a Ric Flair.
I honestly dont know about Michaels. He has actually suprised me over the last 6 or 7 years. Back in '98, when he had his last match with Austin, at the time, I thought that he would take a break for 6 months or so, then return. After he was away for about a year, I thought, "Wow, he really is retired." Then, he returned in '02, which I thought would only be for a couple of matches. But, so far, that 4 or 5 year hiatus, really has added years to his career! I personally think if Michaels retired tomorrow, he would show up from time to time, but I dont think he will take on a recurring role. This time, once he is done, he is done.
'Taker will wrestle his last match then we will never see him again. I honestly feel that he is not one of those "spotlight" kind of guys. He goes out, does his job, and returns to his personal life.
As far as 'Taker giving "the rub" to somebody younger than him. Well, normally I agree with an older wrestler on their way out to "pass the torch" to a younger, active, future Hall of Famer. But, in the case of the streak, there is absolutely NO WAY, they should ever, EVER, end that streak. It would be totally stupid to let him go 17, 18, 19, or 20-0, and end that streak. When 'Taker retires, he should retire where he started, at Survivor Series. I know, "Wrestlemania is the biggest stage of them all. And with 'Taker being as big of an Icon as he is, alot of you probably think his career should end at a Wrestlemania. But, this instance is different. There is not 1 active wrestler on the roster that deserves to end that streak. Honestly, I dont see anybody ever deserving that rub. Not Cena, not Orton, nobody!!