While discussing Bolin's loyalties in Book 4 of The Legend of Korra, a friend of mine made the point that Bolin may have, at that point, spent more time working with Kuvira than he had spent with Korra. I don't think we'll ever be able to say for sure, since we don't know exactly when he joined up with the Great Uniter (all he says in his letter to Korra is that he got a job working for Varrick, and thus presumably joined Kuvira whenever Varrick did).

But do we know how long the first 3 books of Korra took, all told? As I recall, Book 3 started shortly after Book 2 ended, but I can't remember the span between 1-2, or how long the books themselves were supposed to have taken.

By the ceremony scene at the end of Book 3 of The Legend of Korra, how long had it been since Korra left the South Pole during the pilot?

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Based on numerous Avatar timelines found in a Google search, it appears that the time period between the events of the pilot episode and the finale of "Book Three: Change" are approximately one year. Book Four, however, picks up about 2.5 years later.

As you said, we have no way of knowing when Bolin first started working with Kuvira. However, we DO know that Korra spent two years recovering with the Southern Water Tribe after the events of Book Three. Therefore, it seems very possible that Bolin has indeed been with Kuvira for longer than the single year he spent with Korra.

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