Do I really need a 14 day JR Pass

Hi,
It's taken some time, but after many changes, we've finally worked out our travel plans for our first trip to Japan. We will be flying into Tokyo and it would make sense to spend a few days in Tokyo before doing the rest of our sight seeing but we've arranged to meet family who will be in Kyoto for a few days when we first arrive. So our itinerary is as follows:-
Day 1 Narita - Kyoto -
Day 2, Kyoto - side trip to Nara
Day 3 Kyoto
Day 4 Kyoto
Day 5 Osaka -
Day 6 Hiroshima -
Day 7 Nagoya - 1 day
Day 8 Kanazawa
Day 9, Tokyo for 8 days with side trip to Hakone, 5 lakes and fuji area.

Personally, I would spend longer in Hiroshima and Kanazawa but the rest of my group want to spend the lions share of our trip in Tokyo. Even then, they don't think they will have enough time to do all they want to do! Would we best to do a side trip to Nagoya when in Kyoto?
If I get the 14 day pass, can I make use of it to get to Hakone and around Tokyo? We will be staying in the Minato area and will be traveling around Tokyo alot!

Can you please advise me what the is cheapest and easiest way to get around?
Thanks for your time!