I will be in Japan for 37 days total. Have rented an apartment near Saitama Pref. on Seibu-Shijuku line.
Itinerary: Travel to Matsumoto area for 4 days. Will leave from Hachioji Station.
Travel to Kyoto and Nara for 3 days.
Travel to Nikko for 3 days. Will use the Nikko pass for this trip.
Will travel back to Yamanashi Prefecture from Hachioji Station for a couple of days.
All will be done in the order listed. Fourteen day seems perfect except for the last leg from Hachioji Station to Yamanashi area. Less than $300 difference between 14/21 day pass. Hope to hear some of your thoughts. Thank You.
P.S. Arrive and depart Haneda, not Narita.