JR Pass - 14 days - Travel Options

Hi,

I was wondering if it was worth it to purchase the 14 day JR pass for my trip in September and if there were any other travel pass options going from Tokyo to Kyoto. My current itinerary with estimates from Hyperdia (using JR lines) is as follows:

Sept 15 - Narita Airport to Kobe - ¥14800
Sept 16 - Kobe to Nara - ¥1380
Sept 18 - Nara to Kyoto - ¥690
Sept 21 - Kyoto to Osaka - ¥2730
Sept 22 - Osaka to Gunma (+transfer to private rail at Kitasenju) - ¥8510 + additional ¥940
Sept 24 - Gunma to Tokyo (+transfer to private rail at Kuki) - ¥820 + additional ¥630

Total ¥30500 (approx. $380 CAD)
vs 14-day JR Pass $587 CAD

Do these estimates from Hyperdia sound correct or are there additional fees I'm missing i.e. seat reservations? Would it make more sense just to buy train tickets as I go?

Thanks!