Itinerary December 23 - January 6

I'm planning my trip and have a few questions, first here is my itinerary:

Dec 23: leave Honolulu
Dec 24: Arrive Tokyo ( hotel in tokyo)
Dec 25: Tokyo
Dec 26: Kyoto
Dec 27: Kyoto
Dec 28: Osaka
Dec 29: Osaka w/ morning trip out to Nara Take an evening train out to Hakone
Dec 30: Hakone evening train to Tokyo
Dec 31: Day trip to Yuzawa
Jan 1: Tokyo or day trip out to Nikko
Jan 2: Yokohama / Kamakura
Jan 3: Tokyo
Jan 4: Tokyo
Jan 5: Tokyo
Jan 6: Leave Japan

I have a couple questions:
1) Should I get a Japan Rail Pass?
2) Because I arrive so late on the 24th (estimated arrive is 4pm) should I stay overnight in Narita, or just catch the NEX into Tokyo, I'm planning on booking a hostel in Ikebukuro?


Thank you!

1) 7-day Japan Rail Pass costs about the same as a roundtrip on Shinkansen between Tokyo and Osaka/Kyoto. So if you do that roundtrip within a 7-day period, it pays off. Looking at your schedule, activating it on the day you travel from Tokyo to Kyoto would make sense. For Narita to Tokyo, you can buy the NEX and Suica package (good value on travel around/inside Tokyo).

2) 4pm is not late at all. Go ahead and travel right into Tokyo.