Quote Originally Posted by Joel Eade View Post
I think a softbox and the umbrella will be helpful. I would put a flash off to either side of the group at a 45 degree angle just at head height and then maybe one more in front up higher and angled down slightly. The last one up high from the back side with low power just to highlight the edges (hair light). I like the idea of compressing the BG but you will have to be probably 50 yards away with 500 and might be tough to not include your flash gear in the shot.
Joel, Nice ideas, but I need to gang up the lights since I am limited on pocket wizards---since I only have 3 recievers, I will run 3 flashes off of one reciever for the main light, 1 for the fill and 1 for the backlight if necessary. Depending on the sun, I am thinking the main at high left, the fill at shoulder height on the right and the backlight behind the subject/s.

You are dead on about the distance. I checked my old football pics and shooting from the endzone, I could reasonably capture the the backs and 4 linemen at the 50 yard line ---so for a family shot with some background and headroom, 50 yards should be just about perfect. I think I can borrow a bull horn from work