Between the Arkenstone, the One Ring, and that cache of magic swords Bilbo uncovered during Thorin and company’s confrontation with the trolls that just happened to be the former property of the High King of the Noldor, Bilbo and Gandalf’s relationship is just a constant process of Bilbo showing up with some random artifact of world-changing significance and Gandalf sagely stroking his beard and making a pithy remark while internally screaming “WHERE DO YOU KEEP FINDING THESE THINGS”.
Alternately, this is why Gandalf always brings/sends hobbits on adventures. Because if you take a hobbit out of their nice safe holding-pen in the Shire, it will take them approximately ten minutes to stumble across whatever item of world-shaking importance is currently knocking around the vicinity. You take a hobbit out and set them loose and they will find ancient weapons of a godly age, ancient beings that pre-date the world, the one treasure in the middle of a hoard of treasure that you actually need, the single most deadly magic item in the world in the middle of a river, the same magic item in the middle of a cave centuries later, the local magic rock with a direct link to the current villain’s mind (which, in this case, was not necessarily a blessing, Pippin) …
If you put a hobbit down, basically, and there is an item of plot importance within a fifty mile radius, they will put their hand down and pick it up. Guaranteed. (Again, as with Pippin and the Palantir, this is not necessarily a good thing, but at least you’ll know where shit is)
The other reason he always brings/sends hobbits on adventures is that they will also kickstart world-shaking actions if left unattended for more than five minutes. See also: Merry and Pippin toppling Isengard the minute they were left alone near people they could trick into war-slash-mischief. See also: Bilbo giving Bard and Thranduil the Arkenstone in an attempt to negotiate because the dwarves left him unsupervised and somebody needed to at least try and keep the peace. See also: Pippin suborning a Gondorian guard into outright treason in the place of the dead to save Faramir and the Gondorian Stewardship from Denethor’s madness. See also: Frodo, Sam and Gollum royally mucking up Sauron’s everything while entirely alone and unsupervised under his very nose.
Like, it’s a gamble. Taking hobbits out into the wider world and letting them loose unsupervised is not an action for the risk-adverse or the faint of heart. But if you want results in a relatively short time-frame, by the Valar it’s effective.
