14 day itinerary check - pass or individual tickets

Hi
We are 4 adult travellers arriving end of November and I want to check if we should get regional passes or go with purchasing individual tickets. Here is our itinerary:
Narita (arrive)
Tokyo (for 3 nights)
Hakone (1 night)
Kyoto (3 nights)
Osaka (3 nights) - include day trip to Nara and possibly Himejji castle (from either Kyoto or Osaka)
Kanazawa (2 nights)
Nagano (1 night)
Narita (1 night) then depart

Also if we are to purchase individual tickets. Can I purchase these online before we get to Japan? If not, how early do I need to purchase the next ticket for our travels, can I purchase on day or do these need to be bought days in advance?

In terms of regional passes, if we go with this, do we have to pay extra each trip if we are travelling with luggage?

Thank you for your help!