JR National + Regional pass?

Konnichiwa,

We are planning to arrive in HND on 7/11 and depart HND on 7/22.

We will stay in the Tokyo area 7/11-7/16. Then we plan to travel to Himeji for 2 nights (7/17-7/18, visiting Himeji one full day and Osaka one day) and Kyoto from 7/19-7/22, traveling back to Tokyo early on 7/22 for a 16.35 flight (4:35pm).

A few questions:
1. Can we purchase both a JR National pass (7 days) and a regional pass (Kansai or Kansai wide)? We could possibly purchase a JR east pass for Tokyo also (sites including Kamakura, Asakusa, Shinjuku, Tachikawa, Fussa, and Okutama but not Hakone). We would plan to use the national pass 7/16-7/22 to have shinkansen available between Tokyo and the Kansai.
2. If we plan to leave Kyoto early on 7/22, will that leave enough time to arrive in Tokyo, board the Tokyo monorail to Haneda, and process security? I am sorry, I could not find any timetables for the Shikansen options. I believe the Hokuriku arch may be too slow-- is this correct?
3. Are there other suitable options we have not considered?

Thank you!