One possibility is to start both as options and see which you prefer. I work from photographs, so if there is any consideration of both options, I take photographs both indoors and outdoors (whether permitting). This allows for the parent to see the difference and for me to discuss how the photos will translate to a painting.
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Sonia Hale is an award-winning, nationally-collected artist in Boston. She paints commissioned portraits for families and institutions nationwide. Her original landscape and still life oil paintings can be purchased at http://www.soniahale.com. For more information, go to http://www.soniahale.com. You can reach her by email at soniahale1@gmail.com.