help in itinary checking

Hello,

We are a bit confused with the best option to select.
Here is the itinary we are planning to do in november:

Narita Aiport Terminal 1 - Nippori - Odawara (were are planning to go to Hakone actually) - kyoto - nara - kyoto- uji - kyoto- osaka- asakusabashi -Narita Aiport Terminal 1.

Would a 14 days pass be a better option ? or take the train tickets separately. If yes can we buy the tickets in advance ?

Another question I have: how do we go to Hakone ?

many thanks for your help