When to start my 14 day pass

Hello!

I'm visiting for the rugby and wonder when I should start my 14 day pass (if that is the best option)?

I arrive on 10th October in Tokyo Narita
Travel to Kyoto on 15th October
Travel to Oita 18th October
Travel to Osaka 21st October
Travel to Tokyo 24th October
Leave from Narita on 3rd November

Should I get:
7 days for Tokyo (leave on 15th) to Osaka (21st) then get an individual ticket from Osaka to Tokyo?
14 days, to include all of Kyoto, Oita, Osaka? When should I start it?
Does the JR pass work around Tokyo or do I need a separate subway pass for that?
Does the JR pass work from Narita airport?

Thanks so much!!!
Lewis.