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I like your idea Morthoron. The notion of Gandalf and the other wizards wandering the earth as rolling stones is something Tolkien also incorporated into Aragorn's character when he journeyed into Rhun where "the stars are strange" (I love that line).
But for 1,000 years? Or even 500?
It's frustrating that Tolkien didn't elaborate on this period in the Istari history since it was a pivotal time in the Third Age: the long offensive of Angmar and the fall of all three northern kingdoms, the rise of the Balrog in Moria and the overthrow of Khazad-Dum, war and turmoil between Gondor and the corsairs of Umbar and other southern kingdoms. Bad time to go missing.
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