Dec 2015 Winter Japan

Needed opinion and advise on my planned itinerary on Japan (end Dec 2015). Since this will be my first trip to Japan., my main worries include the logistics and orientation of the places I have intended to cover, and especially when days are shorter being winter.

Plan to start the trip from Osaka (Kansai) and completing in Tokyo.
Itinerary as such - Osaka (1N)
- Kyoto (2N)
- Shirakawa-go (1N)
- Takayama (1N) (to Nagoya stn to go Shizuoka)
- Shizuoka (1N in Hamamatsu 1N in Gotemba)
- Tokyo (2N)

(a) Will it be more economical if I purchase the 5 days Takayama- Horuij-ku Tourist Pass - which covers rom Osaka to Nagoya?
(b) Does this Pass allows travelling within Osaka, Kyoto too ?
(c) Also will the carrying of luggage be too cumbersome travelling rail / bus?

Appreciate your advise and suggestions and if necessary to make some changes the my itinerary for a more practical option.

Thank you and best regards.

Travel between Kyoto and Osaka is by Limited Express and not shinkansen. Travel within these cities requires the individual city train/bus pass that is only worthwhile if you travel extensively in a day.

There are spaces for luggage on limited express trains but if your luggage is too large to fit in a plane's overhead compartment then you would have to place it near your seat, eating up your leg area or the walkway.