Chiba - Osaka

Would you be so kind and give my some help about the following travel plan:
Mon 30 sept arrival at Hanada airport - going to Chiba
Tue 1 Oct Chiba - Tokyo - Chiba
Wed 2 Oc Chiba - Nikko - Chiba
Thi 3 Oct and Fri 4 Oct Might do Chiba - Jigokudani - Chiba if not Chiba -Tokyo - Chiba
Sat 5 Oct Chiba - Osaka
Sun 6 OCt Osaka
Mon 7 Oct Osaka - Nara - Osaka
Tue 8 Oct Osaka - Kyoto - Osaka
Wed 9 Oct Osaka - Kyoto - Osaka
Thi 10 Oct Osaka - Koyasan
Fri 11 Oct Koyasan - Osaka
Sat 12 Oct Osaka - Kansai aiport

First I would like to ask if there is any train from Haneda airport to Chiba after 1am (I am arriving at Haneda airport on 30/9 at 00.01am)?

What is your recommendation about buying JRPass - 7 days or 14 days?

I am looking forward for your replay.

Best wishes!