Hi again :D
The JR Pass is valid on all JR lines (including the Shinkansen), local JR buses, the Tokyo Monorail. It is for instance very handy for local travel on the JR Network in Osaka and Tokyo, as most places can be found.
There's not really one time table for Haneda - Osaka as there are multiple transfers. Trains depart at least every 30 minutes and you never have to wait long.
The route basically is Haneda -> Hamamatsucho by Monorail
Hamamatsucho -> Tokyo station by Yamanote line
Tokyo -> Shin-Osaka by Shinkansen
Shin-Osaka, transport to your accommodation.
I would advise reserving tickets for the Tokyo - Shin-Osaka part, the other parts don't have seat reservations.
Hope this helps,