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Need some help with my final itinerary

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We are going to Japan in Nov. This is our second trip to Japan and I am planning to visit some places we did not see on our first trip. Our itinerary is as follows:
Day 1-Arrive Narita and transfer to Tokyo hotel
Day2-Day trip to Kamakura
Day3-Day trip to Nikko
Day4-Sightsee Tokyo (We spent 6 days in Tokyo on our last trip).
Day 5-Take the train to Matsuyama ( about 8 hours)
Day 6-See castle and Dogo Onsen and take the train to Okayama
Day7,8,9,-Sightsee Okayama, Himeji, Kurushiki , Adachi Museum and Gardens, and either Bitchu Takahashi or Onomichi using Okayama as a base
Day 10-Take train to Ritsurin Garden, see garden, and take the train to Hiroshima with evening arrival.in Hiroshima. (We spent a full day in Hiroshima on our last trip)
Day 11-Spend the day on Miyajima and take an evening train to Kyoto.
Day12,13, 14, 15- Sightsee Uji, Nara outlying temples and other sites in and around Kyoto (We spent 7 days in Kyoto and Nara on our last trip)
Day 16-Fly home from Itami

My main question concerns the transportation part of the itinerary. I plan to purchase a 7 day JR pas and activate it on Day 5? This would cover me until I arrive in Kyoto on Day 11.

1-Would a Tokyo Wide Pass make economic sense for days 1-3, or should I just pay as I go for these days? Am I correct that a 14 day JR Pass would not make economic sense for this itinerary.

2- Is the JR train to Kamakura a commuter train with no reserved seats? Any tips on which order to view things in Kamakura, Kita Kamakura and Hase. We plan on being there for about 6 hours, and would enjoy a 20 minute or less walk from site to site, but I can't seem to find walking distances between Hase and Kamakura and Kita Kamakura.

3-Any thoughts or comments on the itinerary or order of the itinerary would be appreciated.

Thanks in advance for your comments.

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