The streak first became something people really cared about during the build to WM21 vs Orton. Having him break it would have been a nice rub and at the time wouldn't have seemed like a terrible decision but in retrospect Orton didn't need it and keeping it alive and turning it into its own spectacle was a dime drawing decision.
After Orton, here's what I would have done differently:
>Have him beat a bigger star than Mark Henry at 22, maybe Kurt Angle
>keep everything the same thru 26
>27 - don't let HHH face him, he already had his chance at 17 - and especially don't have the shit kicked out of Taker the whole match making the streak look weak
>28 - since he didn't beat the crap out of Taker at 27, Taker won't need to face him to get his pride back this year either
>opponents for 27 and 28 should have been any 2 out of: Daniel Bryan, Sheamus, Jericho, Ziggler
>29 [Punk (ufc loser fag that we all now know he is) should have been added to Rock vs Cena] Taker should have faced and beat Brock this year
>30 should have been the year to face Cena (in a proper match)
>After that keep it alive until he's almost ready to retire - have Reigns or Kane break it, then let him come back once and only once after the streak ends to have the cinematic match and beat AJ