10 days Trip

Hi, i have 10 days to spend and need help on the fllwg questions:
1) Ski Resort - Gala Yuzawa or Karuizawa is better? How do i get there from Shinagawa Station?
2) Was thinking of going another city, apart fm Tokyo. Ever been to Osaka. Hence, was thinking either Kobe, Yokohama or another other city nearby Tokyo that is recommended and what are the things to do there? Pls adv transport to get there too.
3) Should i get JR pass or JR East pass?
thanks

1) Ski Resort - Gala Yuzawa or Karuizawa is better?

Gala Yuzawa is bigger and has more snow.

How do i get there from Shinagawa Station?

Take a train to Tokyo Station (Yamanote, Keihin-Tohoku or Tokaido Line) and then the shinkansen to either Gala Yuzawa or Karuizawa Station.

2) Was thinking of going another city, apart fm Tokyo. Ever been to Osaka. Hence, was thinking either Kobe, Yokohama or another other city nearby Tokyo that is recommended and what are the things to do there?

Kobe is nowhere near Tokyo. Yokohama, however, is very closeby:
http://www.japan-guide.com/e/e2156.html

For historical sights I recommend Kamakura:
http://www.japan-guide.com/e/e2166.html

Other attractions near Tokyo:
http://www.japan-guide.com/list/e1103.html

Pls adv transport to get there too.

Each destination comes with an access page with details. Also, the following website is convenient for looking up train connections:
http://www.hyperdia.com/

3) Should i get JR pass or JR East pass?

Not unless you make some long-distance trips out of Tokyo.

A Kanto Area Pass pays off for a trip to Yuzawa or Karuizawa. But the other two passes require more long-distance travel in order to pay off.