Don't worry about shooting too many shots. Take some time to pick a better software tool to help you pick. Picasa offers a great "star" tool that can get you going. BreezeBrowserPro offers a great tool for ranking 1-5, for a modest price. Lightroom (and I believe) Aperture offer all that and lots more in a nice cohesive package for $275-300.


My other suggestion would be simple: get down. Get yourself and your camera down lower - it'll change the background (almost always for the better), and it'll cause the background people to look shorter than your main subject, helping the subject look "important" in the composition. Check Bryan's review pages for the Walkstool, or just bring a folding chair of some form. In shots 2 and 3, think about what would change if you got lower. In shot 4, you'd keep at least the bottom of the fence from going right through head and shoulders.