I'm sorry I don't mean to offend but this is garbage. Nobody in the WWE wants the streak to end. Each year this is debated, each year the IWC storms with stupid ideas as to how the streak should end, and each year the same conclusion is made by the WWE that the streak should not end. The build-up to the match is always done in a way that the streak seems like it is in dire jeopardy, and then the Undertaker finally overcomes all the odds to prove his critics wrong and retains the streak. Despite this becoming a routine over so many years, I am surprised how people still don't learn and still expect the streak to break.
Take a deep breath, and let this sink in - the streak will never break. Yes, face it, the world won't end it Taker retires with his streak intact. Nothing will be lost if he does so. Why will the streak not break? Simple - 1) Taker deserves it, 2) It cannot be recreated.
1) Why does Taker deserve it? Because he has been most loyal to the WWE, he has been the backstage locker room leader and judge of the wrestlers' court, he has handled a lot of issues backstage between wrestlers, he has amassed more respect from his peers than any other wrestler and many other wrestlers including Kurt Angle called him the greatest of all time, clearly stating that is what the WWE wrestlers themselves consider. Taker elevated the bar of performance for big guys and earned/ lived up to the name of the "Phenom" by doing things which nobody else (especially with such a huge body) had done in the WWE earlier, like walking the top rope, flying over it (suicide dive), introducing the tombstone, the casket/ body-bag/ Hell in a cell/ last ride/ inferno matches. He killed Hulkamania, he threw Mankind from the top of the cell to the announce desk below, he flew over the top rope when the ring was surrounded by fire in the Inferno match against Kane, he carried and evolved the greatest gimmick of all time (that too a supernatural one and made it look believable to the fans), he still gives match-of-the-year-worthy performances at Wrestlemania, he crucified Stone Cold, he retired Shawn Michaels, he stayed 18-0 undefeated at Wrestlemania - nobody and I mean NOBODY has had a career like Undertaker in the WWE and that is a damn fact. He never had long title reigns and always gave up the title when it was time for other guys to shine in the limelight like Austin/ Rock/ Lesnar.... feuds with Taker have pushed many guys like Kane, Mankind, Austin, Lesnar, Angle, Orton, Kennedy, Batista, Edge.... nobody and I mean nobody in the WWE has a resume like Undertaker's and so nobody is qualified to end his streak. Shawn deservingly came the closest, and nobody else will get closer. Taker never had long title reigns like his peers had, so the streak will make up for that by being the best "statistic" in his career. If Flair says he is a 16-time champion, HHH says he is a 13-time champion, Edge says he is a 9-time champion, Shawn says he is the show-stopper, then Taker can say that they all fell to him at Wrestlemania. That will be his claim, and he deserves it - let it be.
2) Why can the streak not be created? Because there is no guarantee whether the wrestler who breaks the streak will actually gain enough from it and become as big as the Undertaker did in this business. What is the guarantee that the wrestler who breaks the streak will last as long as Undertaker did, do the kinds of things which Undertaker did, become as big a legend and fan-favourite as Undertaker did, garner as much respect in the locker-room as Taker did, and perform at the level that Undertaker does at this age? What if the wrestler who breaks the streak soon has a career threatening injury and his career ends or shortens so that he is never able to make it as big as Taker? What if he decides to switch companies and joins TNA and brags there about ending the streak? Where will that leave the WWE? The streak is listed as the WWE's greatest record on their records page and it has visibility outside the world of pro-wrestling by being the only streak from this sport to be ranked in the Mirror's list of sports' greatest winning streaks. Surely, the board of directors of the WWE will be angry if the streak ended and the WWE will lose money - the streak won't end, its also business. Its the only untarnished thing left in the WWE right now - why end it? The WWE need a name to quote in history which remained the most dominant and which always delivered at the grandest stage of them all, and there is no better character for it than the dead-man who can't be hurt. Why break something you spent 2 decades to create and when it cannot be recreated? The streak will forever remain a benchmark of greatness and career-accomplishment for young superstars to try and achive something similar to.
It is perfectly fine for Shawn Michaels to lose twice in a row to Undertaker because Undertaker lost twice to Shawn Michaels in '97/ '98 in their hell in a cell and casket confrontations due to interference from Kane. All that Shawn wanted and cared about at Wrestlemania 25/ 26 was to have a good match. So both matches had the right decision. Every wrestler has to retire one day.... similarly Shawn had to, as well. He wanted to retire at Taker's hands rather than some other like cena, not even at the hands of his best friend HHH.... so Taker willingly dropped the title to Jericho at EC and gave Shawn his last match. That itself speaks for the respect that Taker has in the locker room and how much mutual respect Taker/ Shawn have for each other. While Taker defeated Michaels and ended his career, he did not kill Shawn's legacy of being the showstopper and of giving the best match of the night. Wrestlers can beat each others for the title, they can end each other's careers, but they can't kill each other's legacies. Taker ended Shawn's career, not his legacy. Similarly, if the streak is Taker's legacy, nobody will end it. Taker can even retire on a winning note - if Trish Stratus can do it, why can't he?
Shawn will definitely not screw Taker out of the streak, and it is also very doubtful if Taker will face HHH at Mania. HHH has been talking retirement for a while now and it doesn't look like he will go for more than a year, especially with his new executive role backstage as advisor to Vince. HHH has nothing to gain by ending the streak. Taker has better things to do at Mania than retire each and every one of his peers - I hope HHH doesn't face Taker but faces somebody else at Mania. Moreover, the streak should get some fresh names to it rather than repeats of the old ones. I doubt it if HHH will be able to give a better match than he did at Mania 17 with Taker, so there is no point in doing a rematch now.
Instead the WWE can benefit a lot by doing a much bigger match at Mania which will draw much more, like Taker vs cena. It has never happened at Mania before, they are definitely the 2 biggest stars of the company right now, and it will sell like crazy. While cena is a part of Nexus, the WWE has the perfect opportunity to do a gradual heel turn for him and book this match for Mania, revealing him to be the secret leader of the Nexus who orchestrated the attack on Taker at Bragging Rights. The platform is set, the entire story is laid and staring at the face for the WWE to grab this chance, and do it. While it won't be technically as good a match as Taker/ HBK was, it will still be a good match and will fetch a lot of money to the WWE.