Need assistance with itinerary

Hello everyone,
My friend and I are planning our first Japan trip for 2 weeks coming this September to October 2016.
Please give us advice on how to get around Japan. We are trying to figure out if we need to purchase a 7 days or 14 days JR pass. Here is a sample of our itinerary. Please help us out, any suggestion or advice would be greatly appreciated. If you have time, the more details, the better. :) We tried to plan and research online but we are confused and not sure what's the best option for our travel plan. Thank you for your time.

9/25, arrival in Narita airport, Tokyo (check in hotel in Shinjuku)
9/26, Tokyo
9/27, Tokyo
9/28 traveling from Tokyo to Kanazawa
9/29 traveling from Kanazawa to Kyoto
9/30 Kyoto
10/1 Kyoto
10/2 Kyoto-Nara (would like to visit Nara if it's convienent)
10/3 Kyoto
10/4 traveling from Kyoto to Osaka
10/5 Osaka
10/6 Osaka
10/7 traveling from Osaka to Tokyo
10/8 traveling from Tokyo to Hakone
10/9 Hakone to Narita airport, departure after 5:00pm

* We plan to take the limousine bus from Narita airport to our hotel in Shinjuku.
* What option do we have traveling from Hakone to Narita airport?
* We plan to use the forwarding luggage system from hotel to hotel, how much does it cost?
* We plan to rent wifi in Japan for the whole trip, is it pricy?

Sorry, I know we have a ton of questions. Thank you for taking the time to read this post and help us.

Did you post twice with the same questions?

Yes, I posted as guest and then I signed up and reposted again bc I thought it didn't go through. Silly me.

You do not need a 14 day JR pass. You will probably want to get an IC card (a pay-as-you-go card). The IC cards work in many cities around Japan.

http://www.japan-guide.com/e/e2359_003.html

You could fly from Narita (Tokyo) to KIX (Osaka/Kyoto) on your first day using a discount airline. The other option is to do an open jaw set of flights (fly into Osaka, and then fly out of Narita). This eliminates a day a travel between Tokyo and Osaka.

I would do Osaka first, and then go to Kyoto. Look into a bus day pass for getting to places in Kyoto.

Get a 7 day pass, and activate it on October 3rd. Use the pass to go to Kanazawa, Hakone, and Tokyo, and finish the pass on your final day to go to Narita Airport.

Within Hakone, the JR Pass does not help you with transportation. You might want a Hakone Free Pass.

http://www.japan-guide.com/e/e2358_008.html

I have tried to clump together your long distance travel to save on costs. However, you may have a reason, say a festival, for being in a particular city on a certain day.

I hope this helps.

Thank you much for the breakdown. I will look into flying to see how it fits our plan. It's a lot of work to plan a first time oversea trip. Thank u for your help!