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Itinerary & airport help

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I am just about to book flights July 1-14. Does it make sense to fly into Tokyo and out of Osaka?
We arrive July 2nd at 3pm (is it wise to stay in Narita that night and get good sleep and start fresh the next morning to Tokyo?)

Tokyo: 4-5 nights: plans to explore various areas and do day trips to both Nikko and Kamakura.
Thinking of spending a night in Hakone to experience an Onsen/Ryokan (suggestions on where?)
Kyoto: 4-5 nights

Flight departs Osaka (kansai) at 4pm on the 14th (again is it wise to spend the evening before the flight in Osaka rather than Kyoto?. The other option is finding our way back to fly out of Tokyo but that doesnt make sense to me if we are already in the Kyoto area...

JR rail pass: I understand this must be bought out of country and before trip. Will I be able to use it for the entire trip getting to the above spots and around those spots and from/to airports?

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