I'd vote against it unless you are used RHD cars and driving on the left side of the road...

Skiing in Japan is very expensive, and as you said you maybe wasting time as Ski resort are not THAT easily accessible. If you see yourself having other ski opportunities at other countries in the future, then skip it.

Yea I would go with Osaka since you visited Tokyo already but again its your personal preference =]

Osaka
 

I actually lived in Osaka for a good month and a half as a foreign exchange student. I have never been to tokyo... except to catch a plane. So therefore I will say OSAKA! It's extremely nice! Kyoto is just a small distance away. The kansai dialect is fun to hear! The people are SOOOOO friendly and will always have a chat with you or let you know some directions. There are nice tourist like places, AMEMURA, Shinsaibashi, namba, right in osaka. (good for shopping) and OF COURSE the food!!!!!! Osaka has a very different taste in their food... but it is definitely YUMMY! Try going for some of the stands... or the basement malls! Cheap and yummy food. I guess it depends if you want to go more traditional and leisure like... go ahead for osaka (even though their night life is pretty cool too) but if you want more of a tourist and WAH exerience..... with a great shopping spree and cool lights then head for Tokyo...(my host sister loves going there... haha)

Hey i used to live in osaka as well, with my father and grandfather. I will go with Osaka because i had a lot of fun there, the food is awesome, i made afew friends there, and well that was the only part of japan that I've ever been to but when ever i go back and visit other city's i may reconsider..maybe.

I also suggest Osaka area since you have already been to Tokyo. You can also visit Kyoto, Nara, Himeji, Mt Koya and a lot of other sights in Kansai.

I saw a great bunraku theatre presentation in Osaka. If you can catch a show, I highly recommend you go! It's a great cultural experience! Osaka also has great deals on electronics :)

Osaka is a cooler city I'd say. Amerika-Mura, Shinsaibashi and Umeda are well worth scoping out. The punch perms of the chimpira were funny. They thought I was a rebel for being an akage-jin. However, Tokyo was where I had my capsule hotel experience, in Shibuya. Legendary!

Dam sounds awesome!i guess that pretty much settles where=)osaka!

It depends what you like. I've heard that Roppongi is a good place to pick up as many foreigners do. I like the underground system in Osaka, very punctual/efficient.