I don't think we should be too harsh on Gandalf. This is what he says to Frodo about his knowledge:
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Originally Posted by Shadow of the Past
‘A mortal, Frodo, who keeps one of the Great Rings, does not die, but he does not grow or obtain more life, he merely continues, until at last every minute is a weariness. And if he often uses the Ring to make himself invisible, he fades', he becomes in the end invisible permanently, and walks in the twilight under the eye of the Dark Power that rules the Rings. '
[...]‘When did I first begin to guess?’ he mused, searching back in memory. ‘Let me see - it was in the year that the White Council drove the Dark Power from Mirkwood, just before the Battle of Five Armies, that Bilbo found his ring. A shadow fell on my heart then, though I did not know yet what I feared. I wondered often how Gollum came by a Great Ring, as plainly it was - that at least was clear from the first. Then I heard Bilbo’s strange story of how he had “won” it, and I could not believe it.'
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And this is what he says elsewhere:
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Originally Posted by Shadow of the Past
The lore of the Elven-rings, great and small, is [Saruman's] province. He has long studied it, seeking the lost secrets of their making; but when the Rings were debated in the Council, all that he would reveal to us of his ring-lore told against my fears.
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Originally Posted by Council of Elrond
[While hunting Gollum on the borders of Mordor] The memory of words at the Council came back to me: words of Saruman, half-heeded at the time. I heard them now clearly in my heart. ‘ “The Nine, the Seven, and the Three,” he said, “had each their proper gem. Not so the One. It was round and unadorned, as it were one of the lesser rings; but its maker set marks upon it that the skilled, maybe, could still see and read.”
[...] With that thought, I forsook the chase, and passed swiftly to Gondor.
[...] ‘At once I took my leave of Denethor, but even as I went northwards, messages came to me out of Lorien that Aragorn had passed that way, and that he had found the creature called Gollum. Therefore I went first to meet him and hear his tale. Into what deadly perils he had gone alone I dared not guess.’
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Until the hunt for Gollum, Gandalf hadn't remembered the crucial fact that the only unadorned Great Ring was the One. Bilbo had picked up his Ring in a mine of dwarf-fighting goblins; it was entirely plausible that what he had was one of the Seven. Remember that shortly before the Ring, Bilbo and company had turned up three swords of Gondolin in a troll-cave! Given that the High Pass is close to the borders of Angmar, it could even have been one of the Nine. The edge of the Wild is exactly the sort of place the lost Rings might have turned up.
Gandalf didn't go "hey, Bilbo's got a Great Ring that can only possibly be the One, I'll leave it with him and Frodo for seventy-odd years"; he went "one of the Great Rings has emerged; Saruman's ring-lore [that I remember at this moment] tells me it's
not the One, so the only danger is to Bilbo, who frankly seems fine; Hobbits are a resilient lot."
As soon as he remembered that only the One had no stone, he rode directly from the edges of Mordor to Gondor, to check the archives, because he knew that if the One had somehow, impossibly, survived after it was supposed to be destroyed or lost three thousand years earlier, it could be either Middle-earth's destruction or its salvation. He then headed directly back to the Shire, only diverting when Aragorn sent word that he'd found the key witness in the case - Gollum, who then confirmed how the Ring had survived.
hS