Particular Setup of 3 DIDs in one Office

I am new to FreePBX/PBX and I was wondering if anyone had suggestions on how to manage this setup:
We have 6 phones in one office. All 6 phones need to be able to reach each other.
We have 3 DIDs. One is a 949 area code that needs to go to two individuals. These two individuals need to be able to place calls from that 949 area code.
We have a 303 area code that needs to go to one extension and then after so many rings ring all extensions.
We have another 303 area code that we will setup for calling into phone conferences and also DISA.

I completely understand extensions and ring groups, but I think where I might be making things too convoluted in my setup is with trunks and routes. I’m essentially setting up separate trunks and routes for each number (in both FreePBX and VoicePulse FIVE). Is this what I should do? Is there a better way?

you could just set the outbound caller ID per extension in the extension set up and use 1 outbound route to the trunk.

That is to say you could have one trunk to your provider with one outbound route. without having to break down per number. Is this what you’re looking for?

I thought of (and did) that, but I believe that it overwrote the extension outbound caller ID with that of the trunk. When I removed the trunk CID altogether it stopped working.

I do like the feature of having two inbound routes so that people calling into the 949 # get their CID prefixed with something to identify them as West Coast business. Our West Coast “operation” goes by a different name so we need to answer the phone accordingly. Does this create any complications with the setup you suggested?

Is there an advantage to setting up multiple trunks?

You are definitely making this way harder than it needs to be.

Step 1 - Inbound calling and outbound calling are, for most intents and purposes, completely unrelated.
Step 2 - Call your ITSP and make sure they are OK with you sending “foreign” Caller IDs. If they are, use just one outbound route and let the extensions set their own Caller ID. Note that if you phones have multiple extensions, every extension on the phone can have its own Caller ID this way.
Step 2.5 - If your ITSP blocks foreign caller IDs (which sounds about right) you will need to set up three different outbound routes and use the “CID” field in the outbound routes to make sure the right extensions go out with the right CID.
Step 3 - Trunks (which is how call enter and leave your PBX) and inbound and outbound routes are only related - routes use your trunks, so make sure the trunks are working the way they are supposed to, then start messing with the routes.

Hope that helps.