Travelling to Japan for 14 days (Osaka- Kyoto- Nara - Tokyo - Hokkaido)

Hi,
It's really not possible to answer your questions since:
1) You don't say what you've seen or not seen yet at each place in your previous trip;
and
2) What your interests are.

Plus, are you returning from Hokkaido by the rail pass too? Or flying back? You're going to a lot of places for just 7 days.

If you are not so interested in temples and shrines, then you could see just a few that really stand out (if you haven't seen them yet), such as the Fushimi Inari Shrine in Kyoto and the Todaiji Great Buddha in Nara. Some other worthwhile places in Kyoto you might go see are Nijo Castle, the Kyoto Imperial Palace, Maruyama Park, Sagano Bamboo Forest, Iwatayama Monkey Park, Kyoto Station, new Kyoto Railway Museum, Shugakuin Villa, Katsura Villa, and Toei Eigamura Studio. You could also walk through the Nishiki Market, Philosopher's Path, Higashiyama, etc.

For Nara, you could feed the deer in Nara Park, see the Isuien and Yoshikien Gardens, as well as see Heijo Palace, and Naramachi.

One thing you might like is going to see the shibazakura near Mt Fuji. The Hitachi Seaside Park is also very nice in spring.

For Hokkaido, you need to specify what you will go to see. It's a big island.

Good luck.