10 days Itinerary

Hi, I am from Singapore. I love to visit scenic places in Hokkaido. Appreciate if you could answer my question below:

6 Dec -
Arrive Sapporo
Stay a night in Sapporo

7 Dec - 9 Dec (2-nights)
Asahikawa

9 Dec - 11 Dec ( 2 nights)
Shiretoko Shari & Utoro

11 Dec - 12 Dec (1 night)
Kushiro

12 Dec - 13 Dec (1 night)
Otaru

13 Dec 15 Dec (2 nights)
Sapporo and depart on 15 Dec

1) Can please tell me if this itinerary is OK?
2) Need advice on the beautiful scenic places that I should visit in Asahikawa, Shiretokoshari/Utoro & Kushiro?
3) The best routing for these places.

I have no experience driving in winter but I plan to self-drive, is it safe?

Thank you

A1.
Looks Good.

A2.
Mostly lakes and forests.
E.g. Kushiro Lake
Ashikawa is a quiet charming city but not scenic. Biei and Furano and the south has nice plains/farmland.

A3.
Route if fine.
Not safe if unfamiliar. But we all got to learn snow driving sometime somewhere right?

May I know how much (in USD) did you budget for the said trip? I am planning to go to Japan for 10 days as well.

Paul, I budgeted US$1,400 per pax for the 10 days. Budget include 3 star hotel, food and transportation (JR 4 days flexi rail pass + car rental at the train station).

This budget can get lower if you do away with JR Pass, driving all the way is much cheaper and more flexibility. It can be as much as 40% cheaper.

Are you traveling to Hokkaido?