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David-Z,
From reading the replies here I'm getting that your original concern, lighting, had not really been fully addressed. A little bit, but probably not as much as you would like? Here's my take...
Outdoor head shots can be tricky lighting-wise unless you know what to watch out for. The key problem to resolve outdoors is high contrast. A typical sunny day will produce lighting situations your camera can not deal with. It simply does not have the capability to resolve the whole dynamic range from the brightest brights to the darkest shadows. So you have to narrow the range to bring it into something your camera can deal with.
So if you think about it, to narrow the range you must either darken the brightest areas, or lighten the darkest, or both. One thing I do when picking a spot is to try and find a place with already a narrow range. For example, it may be a bright sunny day, but I can shoot the model in open shade at an angle such that the background is the shady side of a large tree.
Next I use my flash(es) to create a nice modeling light on the subject. What I like to do is set the camera to underexpose the background slightly, then depend on the flashes to light the subject. With the background underexposed then a subject in shade is going to be very dark without flash. This can be a tricky balancing act since underexposing a strongly lit daylight background means your flashes are going to have to work hard to overpower it. On head shots it's easier since you can get the flashes in close to the subject.
The problem comes in when you consider that you are limited to a shutter speed that is max sync speed which is usually around 1/200 or 1/250. To underexpose a bright scene with that slow of a shutter means dialing the ISO way down, and then start closing down the aperture. Both of which we know makes the flash work harder.
So a typical bright day head shot for me would consist of two or three flashes, in close, usually the main reflecting off an umbrella. I also like to shoot my 70-200 close to the 200 range and be physically as close to the subject I can be to get the composition I want. This is because a long focal length in close will get me narrow DOF which is usually what I want
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