This diverges a bit from the original question, but I do think that Frodo, Sam, Legolas, Gimli, etc. DID make it to Valinor. Their ship couldn't have been sunk, according to this quote in UT from "Amroth and Nimrodel." (setting: a huge storm has blown up while the ship is still in harbor)
Quote:
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The light Elven-ship was torn from its moorings and driven into the wild waters towards the coasts of Umbar. No tidings of it were ever heard in Middle-earth; but the Elven-ships made for this journey did not founder, and doubtless it left the Circles of the World and came at last to Eressėa.
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Ships that were destined for Valinor (at least those that had the permission of the Valar) wouldn't sink. I suppose Ulmo & Uinen restrained Ossė enough to let them through.