Re: your transportation and accommodation
The JR pass doesn't cover the Tokyo Monorail between Haneda and Tokyo. Tokyo Monorail has been practically covered by Japan Rail Pass in recent years (since the 21st of October 2010).
- Japan Rail Pass: Scope of validity
http://www.japanrailpass.net/en/about_jrp.html#bm_003Anyway, a Japan Rail Pass cannot pay off for your itinerary planned at present.
You get off the Shinkansen in Odawara and transfer to the Odakyu line to get to Hakone Yumoto Station. This line is the train line of Hakone Tozan Railway, which is a company of Odakyu Group.
You may think as if this line were a line of Odakyu Electric Railway, because the Odakyu Odawara Line and this line are jointed in Odawara Station and through train services are available until Hakone-Yumoto.
- JR-East: Maps of Odawara Station(s)
http://www.jreast.co.jp/e/stations/e382.html: You go through first the JR Shinkansen exit gate then the Odakyu - Hakone-Tozan common entrance gate.
- Hakone Tozan Railway
http://www.hakone-tozan.co.jp/en/I'm staying at Namba-Shinsaibashi Osaka & Shinjuku Kabukicho Tokyo Where actually are your hotels?
Namba OCAT is near JR-Namba Station.
(Here "JR" is in the station name itself.)
Namba Stations of Nankai and subway are a little away from Namba OCAT, and Shinsaibashi is a bit farther.
There may be a bus stop for airport limousine buses which is closer to your hotel.
http://www.kate.co.jp/en/timetable/detail/OChttp://www.kate.co.jp/en/timetable/detail/UHBy the way, are you aware that Kabukicho has been known well for its red light district?
I guess that your hotel is in the nearby calmer district (where also Shinjuku City Hall is), but when a kid or a lady is among you travelers, it does not sound the best place for you to stay overnight.
- Japan Guide: Shinjuku; Kabukicho
http://www.japan-guide.com/e/e3011.html#kabukicho