Point: Ric Flair would have an equal amount of high-impact opportunities, given that weapons are not only legal, but an essential part of the match.
Counter-point: Considering that both men can use weapons, doesn't that pretty much keep them on an even playing field? It's not as if Last Man Standing matches are notorious for being constant weapon bashes. Most of the match is still spent executing your moveset until the opponent can't get up. So again, it comes down to that Orton has the higher impact moveset with a Hangman's DDT, running power slam, superplex, backbreaker, RKO, Punt, etc. If you put both of them in the ring for 20 minutes, assuming Flair doesn't make Orton tap before then (which is irrelevant in this enivironment anyway), Orton is going to wear Flair down quicker than the opposite.
Point: Flair is a crazy mufucka that will keep getting up and taking punishment, eventually finding an opportunity to win.
Counter-point: Not actually true. Flair is a crazy mufucka, and he can take one hell of a beating, but he doesn't ALWAYS get back up for me. Case-in-point, their Steel Cage match after the downfall of Evolution. Randy Orton took a beating, including a brutal shot from brass knucks, and still kicked out. Flair took a beating as well, and eventually he fell to the RKO. In my mind, if you can't kick out 1-2-3 in a big match, there's little chance you'll answer the 10 count when there's nothing pinning and/or holding you to the ground. And before somebody makes the comment that Ric Flair was far-removed from his prime by the time that match rolled around, I want to counter by saying that Orton wasn't even close to reaching his prime. He was already the "Legend Killer", but he never became a true face/heel of the company until he became "The Viper" and beat guys like John Cena and Triple H (the second time). When he beat Ric Flair, adding his name to the Legend Wall, he was still somewhat of an underdog.
Point: Flair in his prime would have The Horsemen to back him up, especially with no DQ in effect, and they would collectively be too much for Orton to handle.
Counter-Point: Fair enough... Except that Orton isn't just a meathead heavyweight wrestler. He learned from two of the all-time greats in Flair and Triple H (another point in Orton's favor...). He's just as cerebral as both of them, if not more, and has proven that he can win despite just about any odds. A recent example of this is his WrestleMania 27 feud with CM Punk. Now, in no way am I saying that the New Nexus is even remotely comparable to the Horsemen, but Orton knew the numbers game would eventually get him. ANd so, instead of doing what most dumb faces would do and barrel in there despite the odds, he punted each member of the New Nexus straight to hell, making sure it was just Punk and Orton at WrestleMania. Again, the two teams aren't even playing the same game, but the point is clear that Orton isn't a moron and would have thought of a way to even the odds before this match even took place.
-High impact moves
-Past victories over Flair before his prime
-Beat both John Cena and Triple H at WrestleMania
-Has beaten Shawn Michaels
-Experience faces the best legends in the company
-Experience in Last Man Standing matches
-Can and will even the odds
-Has the Punt in his arsenal, if all else fails
Vote: Randy Orton