Does the 14 day pass save me money?

Hi,

I would like to know which route is covered using the JR pass. Will it save me money or do I buy each ticket separately.

I arrive in Tokyo Haneda Airport in October 9.
October 9 go to Shibu Onsen for one night
October 10 go back to Tokyo for 3 nights
October 14 go to hakone for one night
October 15 do to Kyoto for three nights (with day trip to Kobe)
October 18 to naoshima art island for one night
October 19 to Miyajima sleep one night
October 20 to Hiroshima sleep one night
October 21 to Ōsaka for two night
October 23 Ōsaka to Tokyo Haneda Airport

What lines are covered on my itinerary? Does it make sense for me to buy 14 day pass??