itinery check and JRpass advice

Hi,
We are going to Japan from 31st October and back on 20th November. We are flying to Tokyo and back from Osaka.
We have an active itinerary and we are wondering if this itinerery is good, what rail pass(es) would fit best or should we reshuffle our plan in order to make better use of a rail pass?

Our plan:
31 Oct - arriving Tokyo
1 Nov : Tokyo
2 Nov : Tokyo
3 Nov : AM: to Magome (via Nagiso) - PM: walk to Tsumago - late PM: travel to Matsumoto via Nagiso)
4 Nov : Kamikochte valley (+ maybe Matsumoto castle - outside)
5 Nov : AM: to Nagano/Jigokudani Snow Monkey Park - PM: travel to Ogizawa
6 Nov : 2-day Alpine route: from Ogizawa to Murodo
7 Nov : 2-day Alpine route from Murodo to Tateyama - PM: travel to Takayama
8 Nov : Takayama – Hida no Sato village
9 Nov: AM: Takayama - PM: travel to Shin Hotaka
10 Nov: travel to Ogimache (via Takayama)
11 Nov: travel to Kyoto - PM:Kyoto
12-14 (around) Kyoto
15 Nov: AM: travel to Koya-san
16 Nov: AM: travel to Hiroshima
17: Hiroshima/ island Miyajima
18: travel to Osaka
19: fly back home

Thanks a lot for your feedback!
Liesbeth