Tokyo&Kansai from 30 dec to 9 jan 08

There's so much to see!! Pls someone helps?

This is my idea:
- 4 days in Tokyo
- 2 days in kyoto
- 2 days in a shukubo in koya-san
- visit to a onsen or something similar...

Some questions:
1) Better to stay in Tokyo first and then go to Kansai or viceversa (considering new year's eve...)?
2) Where to stay in Tokyo (low/medium budget but nice!) - hotel/ryokan - wich area is the best?
3) How long in Tokyo? 3 or 4 days is ok?
4) 2 days in Kyoto is ok? Where to stay?
5) Best onsen in this area?
6) Want to stay 2 days in a shukubo... would you suggest? Is there too cold in this period?
7) What do I have to put in my bag?
8) What railway pass do you suggest for my itinerary and how do I get it?
9) Any other suggestion is so much appreciated!!!

Many thanks to all!

Better to stay in Tokyo first and then go to Kansai or viceversa (considering new year's eve...)?

I don't think it matters. The Kansai area has the older temples in case you want to do hatsumode at a nice temple. Tokyo has quite a few shopping centers that will be open on the 1st. Osaka probably, too.

2) Where to stay in Tokyo (low/medium budget but nice!) - hotel/ryokan - wich area is the best?

I recommend a location close to a Yamanote Line train station.

3) How long in Tokyo? 3 or 4 days is ok?

Yes, 3 or 4 days is okay. It depends on how much you want to see.

4) 2 days in Kyoto is ok?

It depends on how much you want to see. Two full days are enough time to visit some of the main attractions. If you are very interested in history and tradition, I recommend to allocate more time.

Where to stay?

You have a huge range of hotels and ryokan of all budgets. Locationwise, I personally prefer to stay close to Shijo and Kawaramachi, where there are many interesting restaurants.

5) Best onsen in this area?

Kurama Onsen in northern Kyoto City is nice:
http://www.japan-guide.com/e/e3933.html

Or Hakone near Tokyo:
http://www.japan-guide.com/e/e5200.html

Want to stay 2 days in a shukubo... would you suggest? Is there too cold in this period?

Yes, it is a good idea. If you bring proper clothes, it will never be too cold.

8) What railway pass do you suggest for my itinerary and how do I get it?

Depends on where you enter and leave Japan. A 7-day Japan Rail Pass pays off if you do a shinkansen round trip between Tokyo and the Kansai region within 7 days.

Many thanks for your answers!