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Interesting thoughts, Huinesoron! I am not sure if I like the theory about Gandalf investigating any possible Ringlords in Third Age.
What is most possible is that when Bilbo found his Ring and Sauron returned to Mordor, Gandalf started to get worried there might be a connection, or possibility that Ring will reappear as his owner is back again. Maybe he wanted to find some scripts about the Ring, maybe he was trying to research something about Last Alliance. I just don't think Gandalf thought Bilbo has The One until long expected party -- Saruman voice just made that thought impossible. I find it weird tho that Gandalf didn't find Isildur's scroll much earlier.
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