Alright so just an update here.

Booked myself the Crowne Plaza Kobe. Going to plan on storing my bag there (unless I can find pictures of the luggage lockers at Kyoto station before then) so I'll plan to leave Kyoto by about 4:30PM putting me at KIX by about 7:15PM.

Looks like I'll do the Kansai area pass wide then buy the additional tag on ticket to Hiroshima and back. I'm guessing the only additional transportation costs I'll have is within Hiroshima (including ferry to Miyajima) and getting around Kyoto itself. I found a few passes for Kyoto but not sure if they're worth it, doesn't seem the buses and such are included in the pass.

Update: Booked the Rihga Royal Hotel Osaka. Will continue looking but its between this and the CP.