Osaka, Naoshima, Kyoto, Magome, Tokyo

Hi Daniel-San,
We are a family of 4 travelling to Japan from 10 April -27 April and have pre-purchased our 14 day JR passes.
We are deciding what date we should activate the passes, as have 18 days in Japan total. Do you think it better to have JR pass for Kansai Airport into Osaka on the first day, or Tokyo-Narita Airport on the last day, with the use of the JR passes in Osaka or Tokyo to get around locally?
Itinerary:
10 April: Arrive Osaka Kansai Airport 7pm, train into Namba on 'Rapt' service?
11 April: Train, return to Namba for the day.
13 April: Train, return to Tondabayashi (south of Osaka).
14 April: Train Osaka to Uno (for Naoshima)
16 April: Train Uno to Kyoto
17-19: Local trips around Kyoto - can we use JR Pass on any subway trains?
20 April: Train Kyoto to Magome
22 April: Train Nagiso to Tokyo
23-26 April: Local trips around Tokyo, staying in Roppongi, ie: not near Yamanote Line.
27 April: Train Roppongi to Narita Airport 7pm.

Also, if we know the longer trip train times we require, what station in Osaka would be good to book all these tickets, once we have activated the JR passes?
Many thanks,
Anne