The cheapest way to go!

Hi! I would like to ask which transportation is the best for me while i'm in Japan for two weeks. Here's my itinerary:
14 august (landed in Haneda) head to Osaka till 18 August
18 August (back to Tokyo) till 27 August.

While in Osaka, we're planning to go to Kyoto as well. Do the JR pass cover up the way to Kyoto?
Which JR pass is the most suitable for me to go to Osaka from Tokyo,Haneda?
And do the JR pass has a schedule of the train? Or the train was always available ?
I have to take note that from 18-23 August, i will go for event which i don't need to use any transportation so if i buy JR pass for 2 weeks it will be very wasted. I will need the train again is on 24-27 include the trasnportation for me to go to Haneda Airport.

Can you give me the best suggestion about my trip? I