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Good points WCH.
I think Tolkien only had a problem with Goldenlocks returning after Numenor fell, as that would put a seeming lot of emphasis on his return -- that is, if the Valar thought it so important that he should return after the removal of Aman [although in Glorfindel I Tolkien mused that Glorfindel returned as a companion to Gandalf].
The Istari were important enough of course. But in any case, before the removal of Aman one could take ship, and yes Olorin would not be in the physical guise of the old sage later called Mithrandir.
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