For some reason I thought (and still think) the best moment to end The Streak was at the Wrestlemania Taker faced "Legend Killer" Orton... now, it doesn't seem that big (in my eyes) as at the point when Orton faced Taker there was a Star in somewhat of a "prime" that was "undefeated" at an event. If Orton managed to end the streak at that point he would've defeated the ultimate legend when he was still on top.
Now, Taker you only see him once or twice a year, so there's not a big storyline that could be done with him and the one who breaks the streak and well, it only serves the purpose of putting someone on the map. (Same thing that beating Batista in his return, The Rock, Stone Cold, HBK, HHH or Lesnar would do.) IMO