hi,
All that can be done very easily , but asterisk to Skype call can be very tricky and may not be guaranteed as this will need the Skype users to be business Skype users,
any user which is not business user may not be contacted via Skype Connect or Skype SIP calls.
Kindly let me know if we can have some chat about the project, so that we both can better understand the need and outcome of the project.
regards,