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A plein air portrait in late fall in Wisconsin is not my idea of fun. Snow, icy rain, wind, leaves blowing on everything, a model who hates cold, and me in a back brace!
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So what's the problem?
(In my entire life I never thought I - Montana raised, Minnesota resident when in the U.S., black-belt hater of being cold - would ever say it, but I haven't seen a real autumn and oncoming winter for a while, much less snow, and gosh, I sure do miss it. (I don't get spring's renewing energies after winter's challenge, either.) Reading your description is almost like hearing the U.S. national anthem played when you're far from home.)
If you're not starting out with reference material that you're in love with and can hardly sleep in anticipation of getting started -- instead of in dread of figuring out how you're going to pull it off -- stop the lesson. Regroup, and simplify. If you want informal, do a photo shoot in the kitchen, or the woodshed. Or focus on the portrait instead of the setting, let the background and context be merely background and context for now. A suggestion can be as powerful as a thesis, if deftly handled.
I have to say that I don't find any images at all posted in this thread. I don't know why -- were there any?. Maybe next time I sign on they'll be there. Sorry I can't speak to specifics.