JR Pass for 15 Days in Japan

1st day: Arrive at KIX airport, Hotel area near Osaka-Namba station
2nd - 4th day: Travelling from Osaka hotel to Kyoto for the next 3 days and back to Osaka hotel by end of the day
5th day: Travelling from Osaka hotel to Nara and back to Osaka hotel by end of the day
6th day: Travelling from Osaka hotel to Hiroshimaa nd back to Osaka hotel by end of the day
7th day: Travelling from Osaka hotel to Himeiji and back to Osaka hotel by end of the day
8th day: Travelling from Osaka hotel to Kobe and back to Osaka hotel by end of the day
9th & 10th day: Travelling from Osaka hotel to FujiQ Highland station as my hotel is near here.
11th day: Travelling from FujiQ Highland to Asakusa hotel near Asakusa Tsukuba Express station
12th day: Free and easy
13th day: Travelling from Asakusa hotel near Asakusa Tsukuba Express station to Yokohama for a day trip
14th day: Free and easy
15th day: Travelling from Asakusa hotel near Asakusa Tsukuba Express station to Haneda Airport

Above is my itinerary and I have a few questions below :

1. For bullet trains, can JR pass cover all the places that I plan to go?
2. For 9th day, how do travel to my destination? Do I need to take a JR bullet train from Osaka to Mishima and then another train to FujiQ Highland station?
3. The JR pass that I am buying is only 14 days and my trip is 15 days, on which day should I activate it?
4. For 11th day, how do i travel from Fuji Q highland station to Asakusa Tsukuba Express station?

Appreciate if you can guide me me.