12 days trip from Nagoya to Tokyo

Hi good morning everyone,
Me and my wife will be travelling to Japan for the first time on 14 – 25 March 2015
with the following itinerary.
Sat 14 Mar Arrive at Chubu Centrair Nagoya 0800
Sun 15 Mar Nagoya day trip to Inuyama
Mon 16 Mar Takayama
Tue 17 Mar Takayama day trip to Shirakawa
Wed 18 Mar Osaka
Thur 19 Mar Nara
Fri 20 Mar Kyoto
Sat 21 Mar Kyoto over night bus to Tokyo
Sun 22 Mar Tokyo
Mon 23 Mar Tokyo
Tue 24 Mar Tokyo
Wed 25 Mar Depart Tokyo 2300
Our questions are: -
1. Is the order of the itinerary ok?
2. Is it too pack/rushing?
3. Is JR pass worth it? If so, 7 or 14 days? When to activate?

Kindly advice and comments as much as possible.
Thank you so much.
Regards,
David Chee

18 Mar might be a bit rush depending what you plan to do in Osaka.
If possible 16 Mar, you could possibly have a stay at Shirakawa-go before going back to Takayama for a night on 17 Mar, one way of doing it.

I doubt JR pass will worth it, since you plan for a night bus to Tokyo.
Nagoya - Takayama = ~6000 Yen
Takayama- Osaka = ~11000 Yen
Kyoto- Tokyo = 13600 Yen
JR 7 days pass might be worth it if you take Shinkansen from Kyoto-Tokyo, otherwise don't bother with it.

You could look at this rail pass that covers trains and buses from Nagoya to Takayama, Shirakawa-go and then back to Osaka.

http://www.japan-guide.com/e/e2361_takayama_hokuriku.html

Thank you so much for the advice and will take into consideration.

Regards,

David Chee