Of course, since we are giving the choice of Hobbits becoming hobbrim at the end, we could always give a choice of Hobbrims becoming Hobbits. (I don't know WHY they would want to become land-lubber Hobbits, but who knows?) Anyway, that would solve the problem of having leaders who would teach the others.
Frankly, I think you are giving "short shift" to the survival skills of the Hobbits. They're tough little cookies, and I bet they've learned quite a lot in the years of their imprisonment. (Ever see that movie "Empire of the Sun"?)
Another issue the three types of Hobbits. Are there three types in the prison, or just generic "Hobbits"? Tolkien suggests some definite physical differences in the three tribes. (Fallohides are prettier. [img]smilies/tongue.gif[/img] ) Did these difference develop after the fall of Gondolin, or were they always present? We've never addressed it in the story. Is Loremaster a Fallohide, Stoor, or Harfoot? What about the brothers? Do they stick to their own kind, or mingle freely? I don't think 75 years is a long enough time to wipe out the physical differences between the tribes.
Going back to the original question. There is a part of me that wouldn't mind just seeing the Halflings go off into the great unknown with a "God-Speed and Good Luck". We don't have to know how they made it, isn't it enough to know that they did make it?
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