vicidial.org

I'd like to be able to use a number of USB 3G dongles to dial out as the sim card in each.

Should be possible, since most of them when connected to a PC, can make texts and calls, then send live through that dongle which is connected to a cellular GSM carrier, associated with that sim card.

Additional bonus, if I can then set each of those available simcard's, each respective phone numbers to each contact, so that I can view which number was used to first contact that person.
Brownie points: If i can then have the dial plan so that it only even calls that lead with that specific number in the future, ie. only use that carrier, for that contact...

I'm looking for a fairly verbose response, since I'm a quite a newbie at all of this...

You'll need to find out how to make them work with Asterisk. Once you have that accomplished, you can use them as trunks in Vicidial. But you MUST start with getting them to work in asterisk.

Oddly enough, the Asterisk user base is much larger than the Vicidial userbase. You should not have a lot of problems finding help if it's possible. You may even find a youtube video! LOL. Note that asterisk is NOT OS dependent. So it does not matter which OS asterisk is running on, the instructions will still work on your asterisk server. IF the asterisk version matches, at least. But: If the asterisk version does not match, don't fret ...bring it here and we'll show you how to "bounce it" through another asterisk server!