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First time visiting Japan. Please help

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We are family of 4 with 2 adults and 2 children, 15 and 11 years old.
I am planning our first trip to Japan with another family. We already have a rough itinerary drawn up. Please help with any suggestions and advice. Many many thanks before hand.

8 days total. We will not buy Japan Rail Pass as we will arrive in Narita and fly out from Osaka. We will stay at Tokyo for 2 nights. We have plenty Hilton points, so to keep our budgets within limit, we stay at Hilton Tokyo in Shinjuku. Will tour major places such as Imperial Palace, Fish market, Edo Tokyo museum and Ginza district. We will get train tickets as needed.

From Tokyo, we will travel to Hakone and stay for 2 nights. We will get Hakone free pass. I haven't found a place yet to stay. This is the place where we want to stay at Japanese style hotel. We are looking to stay at ryokan with private hot springs and bathroom within reasonable price. Please recommend? I have been searching high and low on internet for a place to stay.

After Hakone, we will travel to Osaka using shinkansen to stay at Hilton Osaka in Umeda.
From Osaka, we will make day trip to Kyoto for 2 days in a row.
My question is since we will travel total 4 times to and fro Osaka, do we buy train tickets as needed or is it more worth it to buy train pass such as Kansai Thru Pass?
After Kyoto, if we have time, we might go to Kobe. Any suggestions where to go in Kobe?
Even if we only go to Kyoto from Osaka, is Kansai Thru Pass worthwhile?
Then we will spend the last day in Osaka and will go to see Osaka Castle and Shinsaibashi. Will fly out of KIX.
Thank you so much.

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