Does JR Pass make sense for this itinerary?

Hi, my wife and I are traveling to Japan for two weeks in two days (Monday morning the 14th) from NYC. Assuming there is still time to get 2 passes, would this itinerary make sense?

Oct15 Haneda Airport to hotel/tokyo
Oct 18 Tokyo - Kyoto
Oct 19 Kyoto -Nata-Kyoto (my wife) / Kyoto - Osaka-Kyoto (me to watch Cerezo Osaka)
Oct 21 Kyoto - Osaka
Oct 25 Osaka - Hakone
Oct 26 Hakone-Tokyo
Oct 29 Tokyo -Haneda Airport

If not, should we get a SUICA or Japan Rail or could we buy tickets as we go?
Thank you!