There've been discussions of Bryan taking on The Undertaker at WrestleMania as far back, at least, as the formation of Team Hell No. Over the past 3 or 4 months, I've probably seen several dozen posts and at least a couple of threads mentioning Taker going against Bryan. The idea of Bryan going up against Taker may have been laughable at one time, but that time has passed as Bryan has consistently demonstrated that he's among the top guys in WWE. He might not be as revolutionary on the mic as Stone Cold or The Rock was, but what ultimately matters is the type of response he gets from the fans; and that response over the past 6 months or so has been second to none.
There are pros & cons to having Bryan go against Taker at WrestleMania XXX:
PROS
Match Quality - If there's anybody on the WWE roster who could be counted on to help Taker pull off a show stealing match, it's Daniel Bryan. Whatever limits Taker has in regards to his physical capabilities, Bryan has the capability of helping to carry Taker so that those limits don't really matter.
Fan Interest - The streak has all but taken on a life of its own. It's truly become a major focal point for WrestleMania. Taker is respected by wrestlers and fans alike as a pro's pro. There's also a good deal of nostalgia involved because Taker is genuinely the last of a "dying breed." There are hardly any wrestlers, especially top level stars, who debuted in the mid 80s still around that are able to get in the ring and deliver. The nostalgia isn't a bad thing in this case because Taker can still deliver. It might only be a couple of times a year, but that makes it all the more special. As far as Daniel Bryan goes, a lot of fans respect that he comes off as a down to earth, fearless, passionate, likeable scrapper who can also flat out deliver & make the most of whatever opportunity he's given. As with the aspect of match quality, I think that fans would be able to immediately sense a show stealing match. Fans like both guys and want to cheer for them. If WWE could keep them both as faces that respect each other while building an intense rivalry, then this could be a really big money program.
CONS
Star Power - A downside to this feud is that I don't think that Bryan has the star power at this point to really be viewed as being on the same level as Taker. It's true that Bryan has had fantastic matches with the likes of Cena, Orton, Punk, Cesaro, Sheamus, etc. but Bryan would be going up against the streak. Bryan hasn't had a big WrestleMania moment yet, nor has he scored a singles victory at the big show. His two singles matches were at WM 27 & WM 28 against Sheamus. Their first match was bumped from the main card and Bryan dropped the US title to Sheamus. Their second match ended in 18 seconds with Bryan eating a surprise Brogue Kick and dropping the World heavyweight Championship to Sheamus. Bryan needs credibility at WrestleMania, in my opinion, to really come off as that big time threat to the streak. And while that doesn't automatically negate that Taker vs. Bryan being, potentially, a great match & feud that fans could sink their teeth into, I think that there's a possibility of people saying that something is missing from it. Hopefully, Bryan will have that big moment & win after WM XXX.
The Streak Itself - In some ways, the streak has become something of a double edged sword. The key to making it really shine has been building up Taker's opponent as a massive threat. At the same time, you have some that don't want the streak to end while others are, at the very least, curious about the possibility. If the streak ever does end, it'll be one of those all time great, emotional WrestleMania moments that people will remember in the years to come. If Bryan challenged Taker at WM XXX without that boost in star power & WM success and lost, Bryan would be #22. While he could always say that he put on a killer match against Taker, he'd have still lost. While Bryan isn't on Taker's level as far as star power goes, he's already well above the level in which even jobbing to Taker at WM would be a big rub. If Bryan actually ended the streak without having that boost in star power & WM success, it could come off as underwhelming. Some would see it as an anti-climactic end to one of the best angles in WWE history because of that difference in star power. However, to be fair, you could make a case for an anti-climactic end for damn near anybody because there'll be a lot of people disappointed if the streak ends due to the nostalgia surrounding Taker.
Opinion - From my perspective, I don't think Bryan is ready to go after the streak. I think it could be a killer match that fans could really get into, but the ending of the match at this juncture in time could leave a bad taste in fans' mouths. I'm not sure that there can ever be an "ideal" way in which the streak is ended because if it's ended by someone like Cena, Orton, or Rock, you'll have the complaints of "they don't NEED to end the streak." If it was someone like Bryan, Ziggler or Reigns, you'll have the complaints of "they're not big enough stars to end the streak." Finding that middle ground between being a big star and an overachieving big star is difficult. IF Bryan has a strong & productive 2014 that sees him progressing like he has over the past couple of years, then MAYBE WrestleMania XXXI could be Bryan's opportunity.