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FreeSWITCH?
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Maybe a better idea would be a robocall setup that you would call, hear "record now BEEEEEEP" and rapidtalk your message into it before your allotted time was up, then make calls out to your preset list of numbers that play your message.
There's a lot more to it than that, such as collect call detection, answering machine detection, etc. but it could probably be done. http://www.asterisk.org or http://www.freeswitch.org are your friends.
>My boss and I are running all apple products.
You will be making life much harder for your self if you insist on running a software PBX on apple hardware. I'm not saying you cant, but pretty much everything is designed with Linux as the main target.
>We want an inbound 800# with a Los Angeles. CA tag on it (we're not in CA)
Not sure what you mean, since a toll free number has no localized NPA on it (area code). Maybe you can clarify what you mean by "tag". I use Flowroute as a carrier for my personal phone system. TF will run you $1.25/mo per DID + minutes.
>We want all incoming calls routed to a voice message that lets you pick either myself or my boss. All VMs are to be turned into text and sent to our respective email.
IVR with a vm failover that sends email with recorded atachment - all pretty generic requirements.
>We also want built in capability of faxing and such.
Faxing is best effort over VoIP. You will need to hook an ATA up to a fax machine and have it properly configured to ONLY use g711 for audio codec.
If you are looking to DIY, all I can suggest is that you do a lot of reading, and build stuff in a practice/test environment before you go live.
Some people will recommend you use a GUI, but I think it is much better to learn the actual software you are using.
As far as software goes, I prefer Freeswitch, but Asterisk is also an option.
I've only ever heard of freeswitch, but it seems like exactly what you want. Granted, I've never worked with it, just seen it recommended in similar situations. I think SipGate may also have a similar solution, but I'm not sure. I just use them for my SIP forwarding service to my home phones.