DJing around JP - 7 day Rail Pass

Hello!

I will be DJing around Japan, and would love some thoughts on how best to get around with my 7-day rail pass. It's a bit complicated. We have a friend in Osaka with a car who will be driving us around for the first few days.

Nov 3 - Arrive to Osaka (KIX)
Nov 5 - Osaka // Car with friend
Nov 6 - Takamatsu // Car with friend
ACTIVATE 7-DAY RAIL PASS Nov 7 - Tokyo // Shinkansen
Nov 12 - Osaka // Shinkansen
Nov 13 - Awaji Island // Train
7-DAY RAIL PASS EXPIRES Nov 14 - Train back to Tokyo // Fly back to USA via Narita

OR....maybe we should just get a 14-day pass?!