Japan itinerary, JR pass for 14 or 21 days?

Hello,

I am traveling to Japan in September and trying to figure out what rail passes I need. I am flying into Osaka, arriving September 5th and flying out of Osaka on the 23rd. We are staying in Osaka for half of the trip and Tokyo for the other half (and returning to Osaka the 22nd). I am trying to figure out if it is worth getting the 21 rail pass or if I can manage with the 14 day. Below is my itinerary, however the side trips from Osaka and Tokyo don't NEED to be on the dates listed and can be moved around:

9/5/2015 Arrive in Osaka
9/6/2015 Osaka
9/7/2015 Kyoto
9/8/2015 Kyoto
9/9/2015 Hiroshima/Miyajima
9/10/2015 Nara
9/11/2015 Mount Koya
9/12/2015 Universal Osaka
9/13/2015 Travel to Tokyo, Shop
9/14/2015 Tokyo Shopping and wandering
9/15/2015 Mount Fuji/Hakone
9/16/2015 Kamakura or Nikko?
9/17/2015 Kamakura or Nikko?
9/18/2015 Tokyo Disney Sea or Disneyland - Not sure which one
9/19/2015 Tokyo Game Show - Chiba, just outside Tokyo
9/20/2015 Tokyo Game Show - Chiba, just outside Tokyo
9/21/2015 Tokyo Shopping
9/22/2015 Travel to Osaka and shop
9/23/2015 Fly Home from Osaka

I'm open to any suggestions with changing the above as well. Thanks so much everyone!

My first suggestion would be fly in and out of Tokyo. This is as both Hakone and Nikko has day passes to and fro Tokyo. As compared to the smaller Koya san that takes little time.

My second suggestion is to fly in Osaka and out Tokyo, or the other way around. Making an unnecessary loop means more time and money on travel.

If the above two suggestions are not permissible, a 14 day would be recommended.

Do Osaka, do Koya San, do Kyoto.
Activate JR Pass, go from Kyoto to Hiroshima.
Hiroshima to Tokyo.
Tokyo day trips.
From Tokyo straight to Kansai International Airport.

Hello,

I can't change the flights. I got a really good deal flying in and out of Osaka which is why I went that way. Originally the plan was to fly into Osaka and out of Tokyo but I couldn't pass up the deal. It wasn't until I went to look at rail passes again that I realized the issue with getting back to Osaka from Tokyo.

Hi Stephanie,

Double check me on cost on Hyperdia.com but I believe a 14 day pass will cover your needs. Activate it on 9/9/2015 when you go to Hiroshima/Miyajima and it should cover you to 9/22/2015 Travel to Osaka and shop. That should work with you plans and save you money along the way. The ease of use for this pass is incredible!

I have been to Tokyo DisneySea and it is amazing. If you have been to Disneyland or Disneyworld than go to DisneySea, it is worth it and not like any other parks. IF you want to do both in one day you can always get a starlight pass for one park and a regular ticket for the other. I would also suggest you switch your Disney day to 9/16. The Disney parks are so crowed and the lines so LONG on Friday and Saturday.
9/16/2015 Tokyo Disney Sea or Disneyland
9/17/2015 Kamakura or Nikko?
9/18/2015 Kamakura or Nikko or Yokohama?