Hi! I will be traveling to Tokyo for 11 days in September. I will be landing around 4 pm at Haneda and have my first part of the visit in Osaka-Namba area. I am debating whether I should fly into Osaka or train. I will also be going to Kyoto when in Osaka and for the later part travelling back to Tokyo to finish my trip. The JRPass looks to be convenient as it is unlimited usage for 7 days but I'm not sure if I will be using it that much. I plan to visit all the tourist areas but am unsure if the JRPass will benefit me or purchase subway train tickets. Akihabara, Shinjuku, Harujuku, Tokyo, Osaka, Kyoto, Ikeburo, and Shibuya are all the places I plan to visit.
Tokyo -> Osaka -> Kyoto -> Osaka -> Tokyo

Hi there,
If you can get a connecting flight to Osaka, then that may be the easier/faster/most convenient option. If you are not sure, about your arrival or might want to take a bit of time to relax in Tokyo, then train is better.
It seems you have a lot of local travel, but longer distance is limit to Tokyo - Osaka/Kyoto - Tokyo, with that in mind, normal rail tickets would be the better option.
Kind regards,
Daniel
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