9days at japan

Hi,

I will be arriving at Osaka KIX airport on 13/12/2014 And below is my tentative itinerary.

13/12 - one day trip in Osaka
14/12 - take a flight to Sapporo and spend 3 days 2 nights. Places of interest - fish market, otaru, lake toya and hakodate
16/12 - take flight back from Hakodate to tokyo. 3 days 2 nights at Tokyo including hakone
18/12 - Kyoto - to spend 3 days 2 nights
21/12 - depart from Osaka KIX

1. Is the route okay? Please advise if you think there better route option
2. JR pass necessary? If yes, when should I start activating my JR pass since There are 2 days that won't be covered by JR pass.
3. I want to try out the overnight train to get to hokkaido / out from hokkaido just to get the experience. What are the costs involved? JR pass applicable?

Appreciate your advise.

LPG