OK, tentative itinerary time. It seems that going through Tokyo both ways is easier than travelling one way, so we will be arriving there first. The plan is to do the west first.
Day 1: arrive, pick up JR Pass and wi-fi (JR sells these too, should I get it through them?), get on the train to Osaka, arrive and set up
Day 2: explore Osaka
Day 3: explore Osaka
Day 4: explore Osaka (4 nights in Osaka)
Day 5: get on the train to Kobe, eat meat, stay the night (1 night in Kobe)
Day 6: get on the train to Himeji, visit castle, stay the night (1 night in Himeji)
Day 7: get on the train to Kurashiki, check out the canal area and old stuff, get on the train to Hiroshima (if the weather is shitty on this day, might head directly to Hiroshima)
Day 8-9: go to Itsukushima or explore Hiroshima (3 nights in Hiroshima)
Day 10: go back to Tokyo (is there an overnight train we can take to save on a hotel night and sleep the trip away?)
Day 11-18ish: explore Tokyo (Shinjuku, Akihabara, Ueno, Ikebukuro, Tokyo Station, Yokohama? Roppongi?)
I haven't decided on the arrival day yet so we might stay a couple of days more or less, but I do want at least a week in Tokyo.
We're two old farts (39 y/o) so we want to take our time.