• The Istari (presumably all five) are known to have been in Middle-Earth from (at least) T.A. 1000, though according to later writings, the Blue Wizards arrived in Middle-Earth in S.A. 1600
• The Istari were chosen at the same time according to one text that details the council of the Valar where the choosing occurred.
• > Conjecture: The Istari were chosen and given physical mortal forms in the Second Age, but did not arrive in Middle-Earth together, but were sent/arrived in separate groups between S.A. 1600 and T.A. 1000.
• According to the aforementioned council of the Valar text, the Blue Wizards were chosen as a pair (well, Alatar was chosen and chose Pallando to accompany him), Radagast was chosen to accompany Saruman, and Glorfindel was chosen as companion for Gandalf.
• According to other texts, the Blue Wizards arrived in Middle-Earth with Glorfindel, and Radagast arrived with Gandalf (and possibly Saruman).
• > Conjecture: The Istari did not leave Aman and arrive in Middle-Earth in the same groups. If both versions are true, then there must have been a stopping point between Aman and Middle-Earth.
• 1) The Istari were (at least at some point) commonly mistaken for Elves. 2) The Istari appeared as old men (at least in the Third Age), “but aged only slowly”. 3) Elves presumably only grew beards after many thousands of years (case in point: Círdan), and could therefore presumably not commonly be known by Men to be able to grow beards.
• > Conjecture: When the Istari were first given physical mortal bodies in Valinor, and first appeared before Men, they appeared much younger and were beardless.
• For a long time, Elves of Aman visited Númenor. Among the last of these bore messages of warning from the Valar.
• > Conclusion: The Istari could have arrived in Númenor, perhaps even bearing the messages of the Valar, and been mistaken for Elves

• Five Istari and Glorfindel chosen in pairs in Valinor: The Blues, Glorfindel/Gandalf, and Radagast/Saruman
• The Blue Wizards arrive in Númenor
• Gandalf and Glorfindel arrive in Númenor
• Glorfindel and the Blue Wizards leave for Middle-Earth [S.A. 1600]
• Saruman and Radagast arrive in Númenor
• Gandalf and Radagast leave for Middle-Earth
• Saruman stays in Númenor for some time longer, teaching magic and lore [Bonus headcanon: the man who would become the Witch-King was a student of Saruman]
• Saruman leaves for Middle-Earth some time before the Fall of Númenor
• The five wizards do much to aid the Free Peoples of Middle-Earth in the war against Sauron
• A thousand years later, as Sauron once more amasses power, the Istari declare themselves before the leaders of the Free Peoples, and the White Council is formed. [T.A. 1000]
• Saruman and the Blue Wizards go into the East
• Only Saruman returns from the East

Melkor_Belegurth said:

Hate to ruin your headcanon but this isn't true, the Istari never stepped foot in Numenor, and Gandalf wasn't a pair with Glorfindel.
The different versions are simply Tolkien changing his mind, therefore only one of them is true.

IIRC the final version is:
Blue Wizards + Glorfindel arrived in Middle-earth around 1600 S.A.
Saruman, Gandalf and Radagast arrive in Middle-earth around 1000 T.A.

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Melkor_Belegurth said:

Well, from my understanding, a headcanon is something that wasn't explicitly mentioned in the books, and makes sense lore-wise. E.g: In Harry Potter, my headcanon is that Harry becomes the professor against the dark arts teacher eventually.

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Melkor_Belegurth said:

That is very true, I take more however in a different way, e.g. Bilbo's song about Eärendil: "Then flying Elwing came to him, and flame was in the darkness lit... The Silmaril She bound on him" which is contracting with the Silmarillion - there she only transformed in the morning, where Eärendil woke up to find out the bird is his wife. A different version will be the dates of the Istari arriving to Middle-earth, much like in an earlier version, Sauron was a cat named Tevildo, that's my definition, at least.

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