Asterisk scheduled call to conference

Using Trixbox out of the box, 5 trunks setup with SIP accounts. I am often on the run but at 6:30pm every night i would like asterisk to call me, then on successful connection call a second party (sometimes a third). I would like these calls recorded. I would like to be able to run this on a calandar or scheduler page so i just have to enter the customer i need to call in the calandar at the specified time and then somewhere in an ini file have my phone number. so at the given time in this example 6:30 a call request is dropped in asterisk queue to call me then on my number as entered in the ini file and then upon successful connection call another extension. I am concerned that if the call goes to voicemail asterisk will deem it an answered call so i will need to send a key code down the line to inform asterisk that i am ready to take the conference call. I am not sure if this is best run out of sugar because it has calendaring and click to call or if it is better to start from scratch