Hokkaido December trip

Hi
I am planning to bring my wife and 7yr-old son to Hokkaido this Dec. As its winter and we got a kid with us, we didn't want to rush through some of the places though we could have done some of the places in 1 day or do a side trip. Here's my itinerary with several questions and will appreciate all answers and pointers..

Nov 30 Fly SIN to Haneda, transit to Kushiro
Dec 1 Arrive Kushiro, Lake Akan
Dec 2 Lake Akan
Dec 3 Asahikawa (by the time reach will be late)
Dec 4 Asahikawa (asahiyama zoo)
Dec 5 Furano (winter activity)
Dec 6 Furano (winter activity)
Dec 7 Sapporo
Dec 8 Sapporo
Dec 9 Sapporo (side trip to rera outlet)
Dec 10 Sapporo (side trip to otaru)
Dec 11 Noribetsu
Dec 12 Hakodate
Dec 13 Hakodate
Dec 14 Hakodate

Questions
1. By Dec 1st, will there be snow at Akan? Will the lake be frozen up already?

2. The fastest way by land from Akan to Asahikawa seems to be by bus. Is the bus journey a scenic route, is this the best way other than by air?

3. Should I get the 4 days flexible hokkaido JR pass and roughly which days should I activate the pass or should I get the 7 days pass.

Thanks in advance,

I am Japanese who had lived in Hokkaido until several years ago. Sorry for my clumsy English, but I hope this post might be helpful for you.

1. By Dec 1st, will there be snow at Akan? Will the lake be frozen up already?

Probably　you can see snow at Akan, but the lake will not be frozen (usually begins to froze from middle Dec.)

2. The fastest way by land from Akan to Asahikawa seems to be by bus. Is the bus journey a scenic route, is this the best way other than by air?

It is mountainous and desolate route for over 5hrs. I don't dislike it, but am afraid it might be boring for your son. Unfortunately, Kushiro-Asahikawa direct fright is no longer available from a few years ago. JR line might be another choice, but it also take over 5hrs ride.
If you don't care about the cost, the best choice is taking Kushiro-Sapporo,Okadama flight at Dec 3 afternoon.　In this case, the following route would be modified as Sapporo-Furano-Asahikawa-Noboribetu-Hakodate. Since Middle Hokkaido traffic is much better than that of East, this route should lighten your burden. You can choose a sightseeing taxi as traffic from Akan to Kusiro airport. The driver will guide you to Tantyo-Crane viewing and Kusiro wetter lands before arriving airport (it costs approximately 30,000 JPY for 5 hrs).

3. Should I get the 4 days flexible hokkaido JR pass and roughly which days should I activate the pass or should I get the 7 days pass.

Ordinal fare for using express is listed below (JPY: Children under twelve are half price).
Asahikawa-Furano: 1,040
Furano-Sapporo: 4,030
Sapporo-Noboribetu: 6,680
Noboribetu-Hakodate: 6,490
Sum: 18,240

4 days, flexible within a 10-day period, 19,500 (half for children)

According to your plan, the rail pass is not valuable. If you chose the route I suggested above, the pass saves the cost for a few thousands yen (Asahikawa-Noboribetu: 8,720, 3hrs). 7days pass is also invaluable because it has not child fare.

I hope you can enjoy nice wither vacation in Hokkaido!

wrong Sapporo-Noboribetu: 6,680
correct Sapporo-Noboribetu: 4,360

All listed value includes researvation fee for ordinally cars (except Asahikawa-Furano, it is a local line).

Also, there is children fare for 7 days pass. Neverthelesss, it looks invaluable for your plan.

Hi Kiyoshi san,

Thanks for your recommendation, will check out your suggested iternery.

I need to trouble you all experts again.

1. Do you know if there is any luggage compartment on the JR hokkaido trains?

2. If I have 2 large 27'' luggage will it be easy to travel on the JR hokkaido trains?

3. Will it be better to make use of the takkyubin service? Does all hotels in hokkaido have takkyubin service?

4. If I were to send my luggage from asahikawa to furano or from furano to sapporo or from sapporo to hakodate, roughly how long will it take for my luggage to arrive?

Thanks a million in advance.

Do you know if there is any luggage compartment on the JR hokkaido trains?

Most trains have an overhead rack for luggage. On limited express trains, there is usually also space available for lrger suitcases behind the last seat of rows.

If I have 2 large 27'' luggage will it be easy to travel on the JR hokkaido trains?

I assume 27'' luggage refers to a piece of luggage that measures about 70 cm diagonally, i.e. quite medium sized. Depending on the train type it might fit onto the overhead bin. Otherwise I would go for the last row of seats.

Will it be better to make use of the takkyubin service? Does all hotels in hokkaido have takkyubin service?

Takuhaibin is possible between any place in Japan that has an address, including all hotels. Here are the basics:
http://www.japan-guide.com/e/e2278.html

I am still having troubles imagining the actual size and form of your piece of luggage. But if it is just a single medium sized suitcase, then I would just bring it with me. It also depends, though, on your travel plans and body size. For example, if your plan is to do sightseeing in a way that luggage will cause complications, then takuhaibin can be a good idea even for smaller luggage. But if it is just a trip from hotel A to hotel B with nothing in between, I would just carry it with me.

If I were to send my luggage from asahikawa to furano or from furano to sapporo or from sapporo to hakodate, roughly how long will it take for my luggage to arrive?

It is next day delivery in every case. Usually you can request delivery before noon.

Thank you so much Uji san!!