14 Days Kansai Trip + JR West/Kansai Pass help

Hi, I'll be heading to Japan this week and just need some help on finalizing my itinerary so that I can grab the train passes that I need.

31 May 2016: Touch down at Kansai International Airport, activate JR West Sanyo Sanin Area Pass and head to Kuraishiki to stay for the night. Qn: Can I exchange all the train tickets which I will need for the subsequent days as well?

01 June 2016: Kuraishiki to Onomichi for lunch, to Mihara. I'm hoping to take the Rapid Setouchi Marine View from Mihara to Hiroshima if possible. From Hiroshima, transfer to Miyajimaguchi where I will take the JR ferry to overnight at Miyajima Island.

02 June 2016: Early morning departure back to Hiroshima to visit the A-bomb Dome and grab some Okonimiyaki for lunch @ Okomimura. Grab the EVA 500 towards Fukuoka/Hakata where I will stay for the night.

03 June 2016: Full day @ Hakata

04 June 2016: Hakata to Shimonoseki (Transit @ Kokura) and grab the Misuzu Shiosai (is it operational during this date?) to Senzaki. Take a nice leisure stroll from Senzaki to Nagatomisumi as the next expected train towards Masuda is at 1625? Am open for any recommendations. Once at Masuda, I have to a train to Hamada where I will stay for the night.

05 June 2016: Hamada to Izumoshi to meet up with a friend that's going from Tokyo by the overnight train so that we can head to Izumo Taisha. Is it within walkable distance? Once we're done, head onto Matsue where we will spend the night.

06 June 2016: Explore abit of Matsue and travel to Tottori for the afternoon. From tottori, head towards Okayama for the night. JR West Pass will expired on this date.

07 June 2016: Activate JR Wide Kansai Pass. From Okayama to Himeji (Day Trip) to Kobe for the night.

08 June 2016: Kobe whole day.

09 June 2016: Kobe to Kyoto, possibly dropping by the Suntory distillery on the way.

10 June 2016: Kyoto whole day

11 June 2016: Kyoto to Nara (Day Trip) to Osaka and overnight at Tennojin. Kansai Wide Pass expires

12 June 2016: Here's the dilemma. Do I buy an extra Kansai Pass (3 days) or will one way tickets be cheaper? Planning to travel to Wakayama for an island resort stay.

13 June 2016: Wakayama back to Osaka

14 June 2016: Osaka to Kansai Airport.

Thanks in advance for any help provided!