Re: Unsure where to take shots for a group of 19 people
I think you will be quite lucky to have a great photo of the family without some kind of light modifiers or strobes to give the group a little visual punch. Doing it outside is a great idea since most of your light is already there and as northman said, put the light at an angle so that they are not squinting. I would place 2 flashes on stands just behind and above me. I use Nikon SB800. The sun is already doing most of the work, all you need the flashes to do is add some punch to the group.
The photo with your family in the tunnel of trees is almost there, just needs a little extra from a flash. I would avoid the semi shade as in the last photo because you cannot control where the shadow and sun fall on your subject.
My .02
JimFX
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