Is this even possible with Asterisk?

Background: Basically, all the users of this asterisk setup have two extensions, a regular extension and an intercom extension for click-to-dial scripts and the like. (Phones are Cisco 7960s)

What I know is that I can currently use a call script to use chanspy to monitor anything from one extension. What I want to know is if there is any way in which we can monitor both extensions at one time.

I’ve tried using spygroups to do this (by designating a spygroup in the dialplan for each extension when chanspy is ran on it), but my limited scripting/hacking/programming knowledge hits a roadblock because I can’t figure out a way to designate (without creating 30 separate SIP channels specifically for the various chanspy’s I want to run for each extension) call file Channel destinations without tying up the current SIP channels, in addition to the chanspy channel to monitor the spygroup.

I’ve also thought about dumping the chanspy channels to a dynamic conference for each related regular and intercom extension, but again, my limited scripting/hacking/programming knowledge hits a roadblock.

Before I go to my managers explaining about how my job should pay hundreds for an outside contractor to do this, I would like to know first if what they are asking is remotely feasible.

Thanks,

A frustrated Jr. Network Admin.