Central/Western Honshu using JR pass and hire car

Our desired itinerary is:
4 nights Tokyo
2 nights Kiso Valley
2 nights Takayama
2 nights Kanazawa
4 nights Kyoto
2 nights Osaka

What is easiest way to visit Kiso Valley? Plan to take train from Tokyo to Matsumoto then hire car to spend 2 days in Kiso Valley. Is it best to return car to Matsumoto then get bus to Takayama and on to Kanazawa after a couple of days/use train/keep hire car and drop off in Kanazawa. Or should we be travelling via Nagoya? We then plan to get train to Kyoto and Osaka. Currently not sure if we can fly home from Osaka or may need to return by train to Tokyo so looking at purchasing a 14 day JR Pass. Any comments appreciated. We are travelling October/November.