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Regarded as such only by himself, and his incarnation's physical appearance. Manwe believed in him enough to call only him out, while the others either volunteered, or were brought along upon request.
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I agree. In the Valaquenta, Gandalf/Olorin was said to be the wisest of the maiars. Perhaps this wisdom gave him a sense of humanity, understanding of his own limitations and most importantly the ability to differentiate right from wrong. The other Istaris were most probably chosen for their abilities and powers but I think Manwe chose Olorin because he felt that his sense of righteousness and street-wise would do him credit. Remember, in the Unfinished Tales, Olorin professed that he was not worthy because he knew and felt fear, that was the quality Manwe deemed most important.
As for my thought on this thread, I would like to think of it as Tolkien's way of reminding his readers that not all who shape the way of life must be great and powerful. Very often it would be the lesser beings, the meek ones that would make a difference.