RE: Train reservations during Obon? Well, JR ticket reservation can be made one month before ride at earliest:
for Aug. 7, from 10:00 of July 7;
for Oct. 31, from 10:00 of Oct. 1;
(by Japan Standard Time, UTC + 9 hours).
I have no intention to harm another ticket-booking service as long as it is honest and legal and not law-evading.
If one of you has reached 20 in age and holds a valid credit card of major brands such as VISA, UC, Master Card, then how about JR-West 5489 [goyoyaku] service? This is available for all JR trains if you book and purchase at once on the phone. Sorry if your phone call to the reservation center is rejected because it's from overseas. I think you can still have time to try another in case this service can not accept your language.
At this service, presumably it's OK to have your tickets delivered to your hotel in Japan with 420 to 1,250 yen charge. (For that, purchase the tickets by the day one week before ride).
If that's OK, you have no need to worry when the tickets will come or whether they will come smoothly.
If delivery is impossible, your member who bought them will be required to get them at one of major JR-West stations, presenting the same credit card; so it's better for you to start from Kyoto or Kurashiki to get them.
http://www.westjr.co.jp/english/travel/
http://www.jr-odekake.net/goyoyaku/phone/a.html
(Omit the first 0 in the alternative phone number. Not 078-341... but 78-341....)
(Little slowly to make him/her slow down)
"Konnichiwa (Hello), I have a credit card of VISA. And, yuukou-kigen (expiring period) is January of year two thousands and eleven. I am twenty-five years old. We have xx days before our travel. Can I get my tickets at my hoteru (hotel) in Japan?"
"We are three members. There is no children. / One of us is a child of ten years old. We use Japan Railway Pass. / We need jo'shaken (fare tickets), and we start from XXX on August 7, and XXX on August xx,... and arrive at XXX on August xx."
"We take Hikari Number four-seven-zero from Okayama and arrive at Kyoto at eleven fifty-four."
As a Japanese, I hope JR-West staffers can understand English expressions like these....
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