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Well that's the point in question: if it's Gandalf the Istar it's about 1,000 years into the Third Age, or later... but Nerwende Artanis -- with [in theory] Nenya on her finger -- desires unfading grass, for example? She says this to Olorin before he reveals he has the Elessar.
I don't know why the Olorin idea is necssarily awkward though, as Tolkien himself even speaks to this Maia visiting Middle-earthers very early on, and provides the means. Unless you think the idea awkward even if it's from the uthor, I guess.
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