Like others have said, your planning is really ambitious.

If you can find reasonably priced accommodation and transport to Hokkkaido during the second week of February, then by all means go to Sapporo for the snow festival and then maybe a few days either in Niseko or Rusutsu for ski'ing/snowboarding. With the remaining time I'd say spend them in Tokyo and Kansai, skipping Nagano entirely. (If it was me I would even skip Kansai, and just do Hokkaido + Tokyo).

If you can't find anything reasonable for the snow fest, then skip Hokkaido entirely. Do a few days in Tokyo, then a few days ski'ing/snowboarding in Nagano, then go see the snow monkeys, then finish off the trip in Kansai.