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Why Did 🧙Gandalf Choose Bilbo Baggins?

Gandalf had been visiting the Shire for quite some time judging by his reputation for fireworks and sending adventuresome hobbits on "mad adventures." He seemed to have known Bilbo's mother Belladonna, and had in fact been keeping an eye on Bilbo for quite some time, seeing that he had a strong "Tookish" side and other qualities of interest.
~Gildor

Gandalf wanted to deal with Smaug...the dwarves needed a 14th man...Gandalf wanted to take the stealthy approach..(etc.) So it was the (adventurous) "Tookishness" in him, inquisitiveness along with courage and good heart, that made G. pick Bilbo. That makes sense, since most other hobbits were content to stay in the shire. Now it all adds up!
 
I think Gandalf chose Bilbo because he knew Bilbo would always go on adventures, for a few days and than return. All of the hobbits thought this was quite "queer" because none of them ventured out themself. Another reason was the hobbits stealthness. Only a hobbit could venture into a dragon lair. A dwarf Smaug would have smelt and heard a mile off. But this hobbit kept him guessing, giving Bilbo enough time to get out.
 
Isildur cannot be blamed for not being able to cast the Ring into the fire when he had the chance, because we know for a fact from Tolkien that the Ring's power grows ever stronger as it comes closer to Mount Doom and that on the very edge of the fiery chasm no one could bring himself to destroy it. It is there that the Ring's power to corrup was at its peak.

As for assistance, Gandalf did not "assist" old Bilbo to pass the ring on using any magic, only using that wisdom which a wizard posses. We can, thus, say that Isildur had use of such wisdom himself in his moment of truth through the presence of the High Lord Elrond.

Just wanted to point this out so that you don't get the misconception (which Aragorn had) that Isildur was a weak person.
 

There was "more about him" than anyone knew, except Gandalf. He knew that Bilbo had that Took element in him, and more spirit than the average hobbit. He knew that there was more good stuff in Bilbo than even Bilbo knew.

There is some interesting matter from "Unfinished Tales:"

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The "He" of the opening sentence is Gandalf, "we" are Frodo, Peregrin, Meriadoc, and Gimli, and "I" is Frodo, the recorder of the conversation; the scene is a house in Minas Tirith, after the coronation of King Elessar.

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He would say no more that day. But later we brought the matter again, and he told us the whole strange story; how he came to arrange the journey to Erebor, why he thought of Bilbo, and how he persuaded the proud Thorin Oakenshield to take him into his company.

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(Gandalf: ) Somehow I had been attracted by Bilbo long before, as a child, and a young hobbit: he had not quite come of age when I had last seen him. He had stayed in my mind ever since, with his eagerness and his bright eyes, and his love of tales, and his questions about the wide world outside the Shire. As soon as I entered the Shire I heard news of him. He was getting talked about, it seemed. Both his parents had died early for Shire-folk, at about eighty; and he had never married. He was already growing a bit queer, they said, and went off for days by himself. He could be seen talking to strangers, even Dwarves.

"Even Dwarves!' Suddenly in my mind these three things came together: the great Dragon with his lust, and his keen hearing and scent; the sturdy heavy-booted Dwarves with their old burning grudge; and the quick, soft-footed Hobbit, sick at heart (I guessed) for a sight of the wide world. I laughed at myself; but I went off at once to have a look at Bilbo, to see what twenty years had done to him, and whether he was as promising as gossip seemed to make out.

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'Off again,' said one Hobbit. It was Holman, the gardener, I believe. 'Off again. He'll go right off one of these days, if he isn't careful. Why, I asked him where he was going, and when he would be back, and I don't know he says; and then he looks at me queerly. It depends if I meet any, Holman, he says. It's the Elves New Year tomorrow! A pity, and him so kind a body. You wouldn't find a better from the Downs to the River.' "Better and better!' I thought. 'I think I shall risk it.'

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"But that was not enough for me. I knew in my heart that Bilbo must go with him, or the whole quest would be a failure – or, as I should say now, the far more important events by the way would not come to pass.

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'Listen to me, Thorin Oakenshield !' I said. 'If this hobbit goes with you, you will succeed. If not, you will fail. A foresight is on me, and I am warning you.'

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I do not give my love or trust lightly, Thorin; but I am fond of this Hobbit, and wish him well. Treat him well, and you shall have my friendship to the end of your days.'

"I said that without hope of persuading him; but I could have said nothing better. Dwarves understand devotion to friends and gratitude to those who help them. 'Very well,' Thorin said at last after a silence. 'He shall set out with my company, if he dares (which I doubt). But if you insist on burdening me with him, you must come too and look after your darling.'

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Barley
 
 
Also Spankus, you point out where Frodo hands over the Ring to Tom with seemingly no problem at all. Could that have been due to some influence by Tom, an overlooked instance of exceptionally strong character by Frodo, or an unexplained inconsistency in the Ring's universal ability to corrupt/enslave those who carry it?
 
I think, Baragund, that the ease with which Frodo handed the Ring to Bombadil is due to an influence by Bombadil. Tom asks, or rather commands, it seems, Frodo to show him the Ring. Without a thought, Frodo hands it to him. And yet when Gandalf tosses the Ring into Frodo's small fire, Frodo is just a tad perturbed:
To Frodo's astonishment and distress the wizard threw it suddenly into a glowing corner of the fire. (The Shadow of the Past)
And just a few weeks after the rendezvous with Bombadil, Frodo again shows a dislike of showing the Ring:
 
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