Is my itinerary feasible?

Hi,

I will be going to Japan for the first time in May 2016 and would like to check if my itinerary is feasible.

10 May: Arrive NRT at 7.45am, visit Kanazawa or Kyoto, spend the night at Kyoto
11 May: Osaka day trip
12 May: Kyoto + Osaka (Half day each)
13 May: Hiroshima + Miyajima Island day trip
14 May: Nara day trip
15 May: Himeji and Kobe day trip
16 May: Kyoto
17 May: Kyoto in the day, travel to Kawasaki in the evening, check-in.
18 May: Nikko day trip
19 May: Hakone or Yamanashi (Shiba-sakura Festival)
20 May: Kawagoe, Saitama
21 May: Yokohama
22 May: Tokyo
23 May: NRT --> Hokkaido CTS (By flight, arrive CTS at 7.45am). Rent a car at airport, drive, overnight at Hakodate (with stops at Lake Shikotsu, Noboribetsu, Lake Toya, Onuma Park)
24 May: Hakodate --> Otaru
25 May: Otaru --> Asahikawa --> Sounkyo --> Asahikawa (overnight)
26 May: Asahikawa --> Biei --> Furano --> Sapporo (return car, overnight at Sapporo)
27 May: Sapporo
28 May: Sapporo
29 May: Hokkaido CTS --> NRT flight (Reach NRT at 11.05 am), spend the rest of the day at Tokyo
30 May: Tokyo
31 May: Tokyo in the morning to noon, then to NRT for flight home

Point to note: I intend to stay in Kyoto from 10 - 16 May, then in Kawasaki from 17-22 May and 29-30 May.

I have a few questions:
1) Is Kanazawa worth visiting? Should I head to Kanazawa or Kyoto on my first day?
2) Is my assignment of 1.5 days for Osaka, 2.5 days for Kyoto and approx 3 days for Tokyo sufficient?
3) Should I visit Hakone or Yamanashi on 19 May?
5) Is staying in Kawasaki convenient for travelling to Tokyo and the side trips above?
5) Is 14-day JR worth it?

Feel free to post any comments/ recommendations. Or suggest other day trips from Tokyo to replace any of those listed above. Or if you know of any cost-saving measures!

Thank you so much for your help!