JR Pass or single rides?

I'm traveling to Japan for 17 days.
Will arrive in Narita Airport and head to Shinagawa Station and stay 3 days in Tokyo.
Then will go Tokyo-Okayama overnight, then Okayama-Kyoto, 6 nights Kyoto-Nara-Kyoto, then Kyoto-Hakone 2 nights, (Hakone free pass will be needed) then Hakone-Shinjuku Station, Tokyo for 3 more nights, and back to Narita Aiport.
I'm very confuse if I get the JR Pass or single rides, I'll be traveling between 10 days counting when leaving and coming back to Tokyo, so if using JR Pass I'll need a 14 days.
Thank you very much.

Yes, you would need the 14-day pass at Y46,390, but that looks to be more than the individual tickets. You can use hyperdia.com to price out each journey.

Tokyo Okayama

To save some money, buy a round-trip ticket from Tokyo to Okayama instead of buying "fare" tickets separately. Take care of your itinerary (Tokyo-Okayama-Kyoto-Odawara-Tokyo) to be within validity dates.

Fare 10480 yen, 732.9 km valid for 5 days. Round-trip fare 10480x0.9x2=9432x2 18860 yen valid for 10 days.

http://www.hyperdia.com/en/cgi/en/search.html?dep_node=TOKYO&arv_node=...

Seat fee for Shinkansen reserved seat

Tokyo Okayama 6660 yen

Okayama Kyoto 3980 yen

In these sections you will save 30-60 min each when you take Nozomi Shinkansen which JR pass does not cover.

Kyoto Odawara 4860 yen

Odawara Tokyo 1730 yen

Kyoto Nara Kyoto 710x2=1420 yen

Total 18860+6680+3980+4860+1730+1420=37530

In this case I would recommed you not to buy JR pass 14 days but buy tickets separately. You should buy round trip ticket from Tokyo to Okayama and then add Shinkansen tickets separately.