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8-Day Japan Itinerary

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I’m traveling to Japan for the first time. Below is my Itinerary:
Day 1:13 (Fri) – Arrive Haneda @ 10pm. Check-in in my Hotel in Shinjuku (Tokyo)
Day 2:14 (Sat) – Tokyo (Ginza & Odaiba)
Day 3:15 (Sun) – Tokyo (Shinjuku, Shibuya & Akihabara)
Day 4:16 (Mon) – travel to Hakone
Day 5:17 (Tue) – Hakone. Travel to Kyoto in the afternoon.
Day 6:18 (Wed) – Kyoto
Day 7:19 (Thur) – Osaka
Day 8:20 (Fri) – Nara
Day 9:21 (Sat) – Travel back to Tokyo. Depart Haneda in the late afternoon.

Questions:
1) Is the above Itinerary ok?
2) Is it more practical to buy JR Pass (7-day) with my above Itinerary?
3) For 7-day JR Pass, I plan to exchange it on Sunday (day3) so that the 7-days starts on Sunday (day3) and ends on Saturday (day9), right? I want to use JR Pass to travel back from Kyoto to Tokyo (Haneda). So for my Saturday (day2), I will just use per-entry ticket in the train to tour Ginza & Odaiba. Is this approach practical?

Thanks in advance!

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