Itinerary Check for January 2016 Japan Trip

Please advise if my itinerary is ok.
Any suggestions would be appreciated.

Activate 7 day JR Pass:

Day 1 Osaka to Yanago. Eat, onsen, stay overnight in Yanago.

Day 2 Go to Izumo sightsee, shrine. Eat soba. Overnight Train to Tokyo.

Day 3 Arrive in Tokyo. Go to EchigoYuzawa Sake Onsen. Overnight in Niigata.

Day 4 Niigata to Matsusaka. Eat beef yakiniku. Stay in Matsusaka for 3 nights (bec. Nagoya Toyoko Inn is full.)

Day 5 Day trip to Ise shrines and Toba. Eat lots of seafood. Hopefully grilled abalone in Toba.

Day 6 Day trip to Nagoya and Gero.

Day 7 Matsusaka to Tokyo.

I have combined Ise and Izumo into a single trip before, as well, and I know how difficult it is to combine the two elegantly. I "solved" it by taking a plane between Osaka and Izumo, but it was still not elegant in various ways.

You try to solve it by taking an overnight train to Tokyo. It is not a bad idea if it worked out, but are you sure you will be able to get a reservation for the overnight train? And for the nobinobi compartments in particular?

Note that there is now a flight between Izumo and Nagoya (by Fuji Dream, co-shared by JAL, but unfortunately not covered by the JAL Explorer Pass), which you could consider as follows. It is more expensive than just using the Japan Rail Pass, though:

Osaka - (train) - Yonago - (train) - Izumo - (air) - Nagoya - (train) - Matsusaka - (train) - Tokyo - (train) - Echigo-Yuzawa - (train) - Tokyo

Thanks for the reply, Uji!

This 7 day JR pass trip is actually a portion of a bigger itinerary.
Yes, this trip hinges on the fact I can get an overnight train from Izumoshi to Tokyo. I am hoping my chances are good because I am going on a Tuesday. I can easily switch my plans if I cannot get the overnight spots.

Uji, I also want your opinion on Kaikake Onsen. Is it really superb for the eyes? I have been to Noboribetsu, how do the Kaikake water quality compare.

Do you know if we can reserve train tickets at the Haneda Int'l Airport Ticket office or is this office for JR Exchange Pass only?

Thanks.

Uji, I also want your opinion on Kaikake Onsen.

Sorry, I have not taken a bath there yet.

Do you know if we can reserve train tickets at the Haneda Int'l Airport Ticket office or is this office for JR Exchange Pass only?

I understand that same-day reservations can be made.

Thanks so much Uji.