Japan itinerary check (?regional pass)

HI. we are travelling as family of 4 in few weeks and I think the calculator suggests to get regional pass (kansai hiroshima area) + ?pay for additional trains separately. Could you check below and confirm. Due to travel dates I think we would activate regional pass only on 31/8 or 1/9? (5 days)
26/8- tokyo to hakone (odawara- collect car and drive to hakone)
28/8- odawara to kyoto (?activate regional pass 31/8 or 1/8)
1/9- kyoto to hiroshima (includes trip to miyajima)
3/9- hiroshima to osaka
5/9- osaka to kiso valley (NAgiso)
6/9- kiso valley to matsumato (local train)
7/9- matsumato to tokyo
Thanks for reviewing - assume pass covers kyoto/ hiroshima and osaka but not entry from hakone or to nagiso