regional pass would be better for us?

Hello. It is our second trip to Japan and we do not fully understand how the regional passes work. This is our itinerary this time, how could we do it? Thank you very much for your help:

Day 1 - Flight
Day 2 - Arrival at Kansai airport. Night in Osaka namba.
Day 3 - Osaka
Day 4 - Kyoto
Day 5 - Kyoto
Day 6 - Kyoto, nara and fushimi inari
Day 7 - Kyoto
Day 8 - Lake Suwa and Matsumoto
Day 9 - Matsumoto
Day 10 - Takaragawa onsen (jomokogen station)
Day 11 - Takasaki and Akihabara (Tokyo)
Day 12 - Tokyo
Day 13 - Hakone
Day 14 - Tokyo
Day 15 - Nikko
Day 16 - Tokyo
Day 17 - Tokyo
Day 18 - Tokyo
Day 19 - Return from haneda airport

Thanks