I'm also finding this post very interesting. Many of you talk about teaching your kids to be street smart, and how to size up a situation. OP said that she grew up in a rural area. What if she doesn't feel like she is street smart? that's how I would feel if I lived in the city. I love the idea of raising scrappy, self-sufficient city kids, but I don't know if I'm equipped to teach them what they would need to know. We would be learning together.
Although, I grew up in a small town and I think that gives you a little bit of everything. There were no suburbs or bad neighborhoods. One HS so everyone went to school together. Doctors' kids, country kids, Crips and Bloods, preppies, druggies, jocks - all under one roof.
I really like the PPs idea of telling your kids they can call for a ride home, no questions asked. I need to remember that one someday.