Rail Pass & Tokyo Pass

Hello,
I was wondering if it is makes sense to get the 7 day Japan Rail Pass & 3 day Tokyo Pass for my trip.
(I tried the calculator but I can't figure it out.) I will be in Japan from 10/26 to 11/05.

Itinerary:
10/26 HND airport to Yokohama
10/27 Yokohama to Hiroshima
10/28 round trip Hiroshima to/from Tadano-Umi Station (Okunoshima)
10/29 Hiroshima to Osaka
10/30 Osaka to Kyoto
11/02 Kyoto to Maihama (Tokyo Disney)
11/04 Maihama to Tokyo
11/05 Tokyo to HND Airport

I was also wondering, if I get the 7 day JRP, do I have to activate it at the airport on 10/26 or can I activate it in Yokohama station on 10/27?

Thank you in advance!