About the resume play when the headphone is re-connected:
I started on developing an application where this should be possible. As user of this application you are able to select what should be done (play/pause) when the headphone is connected or disconnected.
Eventualy I want it to be capable of doing more than react on connected headphones. See also:
https://garage.maemo.org/projects/actionmanager/

Currently it does pause the mediaplayer when disconnecting the headphone and start playing again when connected, but this is fixed. No UserInterface is made yet for changing settings.

Unfortunatly I havent been able to upload this to the repository yet. So be patient...