Who Wields the blade might just affect the Keychain born. Cases in point - Aqua and Riku vs. Sora when coming in contact with Kairi.
So I think there somehow would've been a higher chance for it being proper X-Blade influence had Riku had the KK on his lonesome too, rather than it being the Ven-factor.
'-' it makes sense in my head at least.
Who says that this particular keyblade wasn't always the KK? The KK is, after all, that keyblade's true form.
As far as I remember the smashing of the x-blade caused everything sans the LS in the Keyblade Graveyard to be swept into the lanes of between, so would also be the remains of the x-blade (if there were any, which I still doubt). So one of these remains remained in the RoL and degraded to a normal keyblade, the KK, while the other part of the remains sank into the RoD and became the dark counterpart of the KK.
I seem to have missed those quotes if that's what you meant. But even Nomura said that as far as the Wielders we know go, Sora's the only exception to the Rite of Succession ceremony. So that means Ven and/or Vanitas were why he managed to Wield.
Duel Wielding would come from there being two Wielding Hearts with two Keyblades. And by that point I think it's safe to say Sora became a Wielder by his own right, so it's all good.
It was, if I remember right (sadly that site is down atm so I can't check) another interview of you-know-who where he was asked if Sora could wield because of Ven. He denied it and said the ability to wield was Sora's own, as all conditions for wielding a keyblade are not yet revealed. A strong heart is needed, that's the obvious one, and this inheritance ceremony makes a individual a chosen wielder which
guaranteed to wield one in the future if the heart is strong enough. Though I don't remember it's being said one needs the ceremony to wield at all. If a keyblade decides one is worthy to be its wielder it doesn't matter if there was a ceremony before or not.
that's why Riku could reclaim the KK from Sora, he had the strong heart and the ceremony, which Sora lacked. Also it might be because of this he gained the Way to the dawn, his true keyblade, later.
As for how Vanitas plays into this...I dunno, I only have a feeling that we're not yet done with that black-haired troll-twin of Sora.
Well, what maybe could be the case is that the keyblade sensed that Sora is harbouring and protecting the injured heart of an already chosen wielder and it therefore decided to go to Sora, but again, speculation.
That's yet another reason why I said a lot of it depended, on my opinion, on who it was that Wielded first. Riku'd be "impressioned" with the KK's design. Also, there's a double bond at work here - it being his own Keyblade to begin with so he might've just been able to use the Keychain, or - his own unexplained, highly likely tie to Vanitas. Not only will it strengthen his bond to Sora, it will also form a bond between him and the X-Blade.
Lol, who knows, maybe that KK we saw Riku use wasn't Sora's KK Keychain but Vanitas's. Now won't that be a hoot?
It still leaves the KKD to be the "Match" though '-'
Then we would have two KKs and one KKD...uuhh, where's the second KKD *gasps...you don't mean...Aqua? Ansem the Wise* lol...
Actually I think there comes it where you think too deep...I just assumed the KK is that particular keyblade's true form, regardless who wields it.