Just curious derrel, why would you not want to put the flash opposite the sun? The subject will have a nice rim light from the sun, the trees in the background will have the shadow face facing you, the subject will not squint looking at the sun. If I turn off the flash, this set up will yield a nice photo too. I want that dark background.
I think you're totally mis-reading what I wrote. I specifically discussed a situation in which there are shadows cast one way in the background, and then shadows cast by a flash that lights the foreground from the opposite direction; when there are background shadows going in "one direction", and then foreground shadows go in the opposite direction, it looks like a noob shot it because the lights are in direct conflict with one another. That looks amateurish, at best, and ridiculous at worst.
I know what you mean; you're talking about today's fairly standard outdoor portraiture shooter's method of using the sun as a rim-light/back light/side-light source, and then using flash as a way to fill-in the shadows: position family at X spot, with sun behind or off to the side: fill in shadowed side with flash to create basic light source for faces,which are in shadow, allow the over-exposed edges of the people to create a bright, separation light; bonus points if background has a dark area so that family stands out more.
Two totally different situations.
Another example of a lighting mess: Joe Photog lights background with light blasting in from one side; lights subject with light coming in strongly from opposite side. Hair light appears from opposite side of main light. Photo looks like a confused mess. Light blasting in from three directions. It just looks contrived, or faked...