Itinerary regarding a14 day pass

Hello, I am inquiring about a 14 day pass for 4 adults for October 14 to 29, 2025
Our travel plan is as follows:
Narita airport to Tokyo Oct 14
Use pass within Tokyo for Oct 14-17
Tokyo to Hakone via Odawara station then Hakone pass Oct 17
Odawara station to Kyoto October 19, Will use pass to go from Kyoto to Osaka and back 2 times
Kyoto to Hiroshima Oct. 25
Hiroshima trains within city and to and from Miyajima
Hiroshima train to Ueno on October 27
Travel to Narita airport on October 29

Is a 14 day pass suitable for this itinerary.?
Are there long line ups to purchase individual tickets? if we do not purchase pass.
Can we book reservation ahead of our arrival to Japan for Narita express to Tokyo.?

Thank you. Donna