Tokyo - Osaka / Kyoto - Hakone - Tokyo

Hi there, would appreciate if anyone can help me on this route planning.
Below is my planning for 4 first time adults traveler to Japan.

Place we wish to cover is Tokyo, Mount Fuji, Kyoto, and Osaka.
Our travelling date is as per below:

Plan A:
17th Oct 2015 - Haneda Airport
(we will be arriving late, so am planning to spend time in airport, depart next morning when monorail start operating again to Shinjuku) 18th Oct 2015 - Haneda Int. Airport - Shinjuku - Osaka
19th Oct 2015 - Osaka
20th Oct 2015 - Osaka to Kyoto
20th Oct 2015 - Kyoto - Hakone (possible?)
21st Oct 2015 - Hakone / Fuji Five Lakes
22nd Oct 2015 - Hakone to Tokyo
23rd Oct 2015 - Tokyo
24th Oct 2015 - Tokyo
25th Oct 2015 - Tokyo - Haneda Int. Airport - Malaysia

Plan B:
17th Oct 2015 - Haneda Airport
18th Oct 2015 - Haneda Int. Airport - Shinjuku - Kyoto
19th Oct 2015 - Kyoto
20th Oct 2015 - Kyoto to Osaka
20th Oct 2015 - Osaka - Hakone or Fuji Five Lakes
21st Oct 2015 - Hakone / Fuji Five Lakes
22nd Oct 2015 - Hakone / Fuji Five Lakes to Tokyo
23rd Oct 2015 - Tokyo
24th Oct 2015 - Tokyo
25th Oct 2015 - Tokyo - Haneda Int. Airport - Malaysia

Which route will work more good and is it a good deal for us to buy 7days JR pass?
Appreciate if you can comment me on this planning. :)

Arigato.
Regards, amane