Osaka, Kyoto and Tokyo 16 day itinerary

Hi everyone!
I'd like your opinion on my 16 day itinerary to Japan this year during November and December as I'd like to see the red leaves this time round as I had just missed the leaves last year. I've already booked my accommodation in all 3 cities and I plan to travel with a 14 day JR pass.

Day trips:
Osaka accommodation
22/11 - arrive at Kansai at 7.20am -explore osaka using 2 day osaka pass
23/11 - osaka 2 day pass
24/11 hiroshima + miyajima (start date of 14 day JR pass)
25/11 himeiji + kobe
26/11 arashiyama

kyoto accommodation
(Ifll be staying near fushimi inari shrine)
27/11 eastern kyoto: Kiyomizudera, Higashiyama Streets, kodaji temple, gion
28/11 northern kyoto: kinkakuji, ryoanji, ninnaji
29/11 asuka or nara (havenft made up my mind yet)
30/11 korankei
01/12 okayama

tokyo accommodation
02/12 travel from kyoto to shinjuku, drop luggage at hotel and do 1/2 day - kawagoe
03/12 kamakura
04/12 Rikugien garden, asakusa temple, ameyokocho
05/12 gotemba outlet
06/12 shibuya, harajuku, akihabara
07/12 disneysea tokyo
08/12 leave tokyo at 9am

Also do you think I should get an ICOCA pass for all the non JR lines just so I could eliminate the hassle of buying tickets?

I'd really appreciate all your opinions and suggestions :)

Thank you!

An IC card is definitely recommended, it will make travel on the non-JR lines much less of a hassle!

Okayama is closer to Hiroshima than Kyoto; maybe consider moving Okayama up a bit.

Have you checked to see if the 14-day JR Pass will pay off? Are you flying out of Tokyo or Kansai?

Thanks for your reply sq!
Ifve calculated the fares using hyperdia and the 14 day JR pass just about pay offs with all the side trips Ifll be making.
I was initially planning to go to Okayama on the 26/11 but was worried I might miss the red leaves at Arashiyama so I moved it further down. Can you please suggest any places closer to kyoto to visit instead of Okayama?