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It looks like the rail pass will pay for itself based on your schedule. Just one note, even though you have the rail pass, you will still need to go to the ticket window and have a seat assigned to you. You will not be charged, but by doing so you have an assigned seat. for local JR train rides, you can just present the pass to the ticket gate person and he/she will let you pass through.
Tokyo – Kyoto 13100 yen
Kyoto – Osaka 8370 yen
Osaka – Okayama 6260 yen
Okayama – Kobe 5840 yen
Kobe – Tokyo 14870
Total = 48440 yen
convert to GBP and you have about a pound difference at 331 GBP.
The advantage of the pass would be the fact that all of that travel cost will be covered and you will not have to worry about that.