Bb, thanks for the kind words!
I agree with you William Cloud Hickli. Tolkien was so opposed to the idea of Empire that I don't think this was part of the equation.
My gut feeling is that hobbits were chosen, but "chosen" in a more limited sense. Their particular combination of strengths and weaknesses made them perfect for a mission that required secrecy, endurance, pluck,and a natural aversion to projects requiring great ambitions. Even beyond the choice of the hobbits as a people, there was also the element of choice that came into play when the particular individuals were chosen for the job. Most stay-at-home hobbits were too complacent and lacking in imagination to go on a quest of the type that Bilbo and Frodo did. These two were chosen because of two apparently contradictory reasons. On the one hand, their lives embodied many of the strengths and weaknesses of the hobbits as a whole; on the other hand, both were non-conformists who rejected many aspects of hobbit life. Both elements had to be there.
It wasn't so much the designation of a chosen people but finding the perfect individuals to take up a particular job. Still, my gut feeling is that for a very long time it was clear that a hobbit would have to be the one to do something like this. Gandalf was the critical factor here. He had to look over the community and study it to find which individual(s) would be the best. If he had made the wrong choice, there would have been disaster. We've always assumed that Gandalf made the choice on his own to spend time with Hobbits and study them. Yes, that is possible. He certainly liked them. But it's also possible that he knew from the time of his arrival in middle-earth that part of his job was to get a closer look at the hobbit community so that he would be prepared to make a choice when and if the time came.
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