I don't think this is just about where you sleep, and it can't be a backyard camp-out. Those folks don't know if they'll be safe, they don't know where there meals are going to come from or how they'll wash or any number of other things I don't have a clue about. It's not just about the sleeping situation. I also think you may find something good out there, because it seems like you have friends.

I would, however, just let the cops know you're going to do this and see if THEY have any tips.

On the other hand, how will this experience help you? At the end of the day, you know you have a home to return to, and that may be one of the hardest things about being homeless: no safety net. No temporary "field trips" will let you feel that, but perhaps the people you work with would respect that you made the effort, regardless.