Hi,
I do not know of a solution for the first item, but the second can be done within the Asterisk dialplan using the DIAL command - to quote from Asterisk Wiki -
Dial - "Attempts to "dial out" on all the specified channels (each specified by a
type and
identifier) simultaneously. The first channel that answers "wins", and all the other outgoing channels are hung up. The originating channel that triggered this Dial command is then
Answered, if necessary, and the two channels are connected together ("bridged") allowing a conversation to take place between them. When the channel that triggered the Dial command hangs up, the Dial command exits."
Asterisk wiki -
http://www.voip-info.org/wiki/view/Asterisk+cmd+DialRegards
Paul Adams