The Enclave thing is quite uncanny. It certainly wasn't intentional, though I must admit I was (and still am) a great fan of the Fallout series (though may of course have had such images stuck in the back of my mind for the last 10 years).
It's more likely to have been mostly coincidental, perhaps by going about things in a similar manner. Basically, when looking at doing the race logos and flags, I tried to look at historical and recent developments in different flags and things, then tried to work out "likely progressions" according to Dave's suggestions relating to the storyline or structure. In effect, they're all thematic derivations from existing logos and flags, which are hopefully "possible" variations... to a degree at least...
That one (and the allies themselves) actually came from something akin to the U.N. - though as they were no longer based on Earth as a collection of nations, but a collection of different planets of people, I replaced the "flat earth" with a circle of stars, with a bigger one in the middle for "remembering their common homeland". As (by earlier storyline at least) the US were the only nation remaining on Earth after this point, it is they who have a "flat earth" based embellishment upon a developed stars and stripes flag.
Regarding the portraits themselves, I cheated a little bit for the faces. The basic faces were done in a trial version of a program called "Facegen modeller" (http://www.facegen.com/modeller.htm), which allowed the variations for happy, neutral, angry etc, with semi-realistic human heads. This came out with bald badly lit floating heads.
The clothes are mostly taken from odd photographs or some from just google image search, and some of the backgrounds are made (very simply) in Wings3D http://www.wings3d.com/ with the Yafray renderer. The rest of it all is Photoshop 7 (might be 5 years old, but it still does the job).
The faces are heavily photoshopped, the hair is drawn by hand (or mouse, I suppose), the clothes are photoshopped, as are all shadows, dirt, stubble etc. The backgrounds are either entirely manufactured in photoshop, or a combination of photoshop and Wings3D models. The happy, angry and neutral faces are all pretty much the same, except the facial expression. Most of the rest stays where it is.
They're also subtly animated (but only as far as light flashing like being-in-front-of-a-video-screen-type-lighting - there's no figure movement), which was done simply in the RAD Video tools thing for converting them into .bik videos.
When I've got all these ready for the TBL mod, I'll see about typing up a tutorial thing for this style of character screen on the i-mod site. I am also in the early stages of doing some "proof of concept" test "proper" 3D rendered and animated alien chaps, hopefully for the New Frontiers mod, which if they work (and they seem to be going okay so far), I'll see about doing a tutorial for those too (though that will be a lot later on).