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Jean:
A plein-aire portrait, WOW! Sounds like it will be a great but challenging start to painting from life. I might recommend simply pulling her inside for a few sessions beforehand and doing some head studies. Put her next to a window (north if possible) and do a few studies from life. That will give you a lot of information about her facial structure, proportions, coloring, etc. It will also show you how wonderfully natural light models the form and give you an idea of what you will want to look for in your outdoor setting.
You are going to have a challenge painting her outside as you will be seeing a constantly moving target with the light changing as the day goes on.
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