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How difficult will it be to setup multiple phone numbers for different groups of people. When someone calls a number it should ring my phone. When I call someone it should show the caller id as being the number for the group the given target is in.
Assuming that you want to setup a mini call center like system in Asterisk ,
It is easy to an extent , if you are familiar with Linux and IP telephony ,
Here is the tutor which I had tried long back . IF you want to familiarize yourself with Asterisk you can follow this tutor