I think the point of all of this stands with the question: "Who the ents really
were?" Because this is it. Let us take a peek in the Silmarillion, chapter 2. Here Yavanna comes to Manwë for advice, because she is worried about the fate of the trees when the Children of Eru Ilúvatar (the Men and the Elves) - and now also the Dwarves - come. Manwë in turn asks Eru for advice.
Quote:
Then Manwë awoke, and he went down to Yavanna upon Ezellohar, and he sat beside her beneath the Two Trees. And Manwë said: 'O Kementári, Eru hath spoken, saying: "Do then any of the Valar suppose that I did not hear all the Song, even the least sound of the least voice? Behold! When the Children awake, then the thought of Yavanna will awake also, and it will summon spirits from afar, and they will go among the kelvar and the olvar, and some will dwell therein, and be held in reverence, and their just anger shall be feared. For a time: while the Firstborn are in their power, and while the Secondborn are young."
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This is all about the beginning of the Ents. "Eru will summon spirits from afar" - I don't know if we are talking about ainur-like forms here, or if Eru "summons spirits from his sleeve", some totally new creation, but the point is, that they are spirits. "And they will go among the kelvar and olvar" - meaning
Animalia and
Plantae, respectively :D "and some will dwell therein" - this means, these spirits will "merge" with a living body (of a tree, or an animal). Note also that here, we are not informed just about Ents ("among olvar") but also about some spirits which, possibly, have come to dwell in animal bodies (in this case, the Eagles or, e.g. Huan). If we are to venture a little bit further, it is quite likely (and I am quite inclined to believe this) that there might be very much more of these "spirits" - whatever they were - and from here all the Dragons, Werewolves, Barrow-Wights (! ;) ) and all this stuff comes (be they just "some remaining spirits who did not find a body fast enough and were trapped by Melkor" or whomever Melkor has called in his early days, somehow being given the authority to do this, or be they Maiar who joined Melkor and Melkor trapped them in the wolf, dragon etc. bodies).
But I got a little bit off-topic. The point was, that Ents were not "fully valuable beings" in the same way as the Men or the Elves were, they were much more similar for example to the Wizards or the Eagles or whatever. Thus, I'd say there'd be nothing against them resting in Valinor, but since it seems their place was out there in Middle-Earth (as "the guardians", not in the Undying lands, where such things were not needed), and I can't imagine an Ent flowing across the Sea, it would seem, homm, hmm, they had to wait. Perhaps they became treeish (I find it quite likely), the "fire (if such a word is in place in case of an Ent) of the spirit" has faltered inside them, and so they are still here, around, but not distinguishable from other trees... only, maybe, older and more interesting at look... but until the drowned lands rise again, they won't awake and they won't be seen at dusk in the Men's realm.