High heels, do the benefits really outweigh the setbacks? All the women I see wearing them just look like...?

It's a personal choice and yes they can hurt. The key is wearing them occasionally. As a short woman the positives are height, power and a y look. When I wear heels men take notice and my day seems easier. (My boss is a male) I work with a tall woman, who occasionally will wear them, and she enjoys towering over men. So go figure...