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If I had to choose between the two, I would plump for Merry as the more contemplative and mature of the two. But I agree with your idea, akhtene, of the two of them accomplishing the Quest as a team, although one of them (Merry?) would have had to have been the actual Ringbearer.
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An interesting speculation, Saucepan Man! Merry does seem to be the more mature of the two of the hobbit pair; but I've noticed something else about Merry. He needs someone or something to love and protect. He seems lost when Pippin goes off the Minas Tirith; he misses Pippin terribly, and he latches on hard to Theoden and the Rohirrim. He seems to be extremely passionate in this regard, more so than Pippin, who, although loyal and steadfast, is much more the risk taker and active component of the pair.
I shudder to think of the depths of despair that Merry would undergo if he were to bear the Ring, but I know that Pippin would bear up with him. I do not know whether Pippin would have the same discretion and intuition that Sam has when he is called upon to act alone to carry the Ring and save Frodo. Pippin seems to have a charmed life, and he seems to happen into revealing experiences, so it might be fortuitous for this combination to occur. He also resists falling into the depths of despair, viz. the Pyre of Denethor and his wish at the Gate of Morannon that Merry could be with him. I do think Pippin could keep Merry going at the end, and I also think Merry would require it, same as Frodo did from Sam. So, yes, I could see it happening.
I do wonder what would happen at the end, when Merry stands at the Sammath Naur and claims the Ring for his own...the wild card of Gollum of course is unaccounted for in my speculation. I do think that, in the end, Pippin would take Merry and the Ring with him into the Mountain of Doom, just as I believe that Sam would have taken Frodo in had the worst come to the worst in that sense. The wildcard is Gollum, and it would take someone of Frodo's sensibilities and sensitivity to deal with such a factor. I'd say, without Frodo or Gollum, you'd have some dead hobbits in this affair. And I'd hate to see that! (I'm one of the ones who can't bring myself to play Hanghobbit!)
Nice theory though!
Cheers,
Lyta