I do most of my flying around downtown, and around the train yard and the silos there. On the "legally" note, check out a recent lawsuit back east regarding the ability of the FAA to regulate hobby flying, Taylor v. Huerta. The court discusses the legality of the FAA regulations. Also look at United States v. Causby, which sets the limit of how high a landowner's property extends into the airspace.
Disclaimer: I am not a licensed attorney and everything I say in this forum should be taken at face value, and nothing, express or implied, establishes an attorney-client relationship, nor is it legal advice, and should not be taken as such. As a law student, I am able to tell you what the law is, but not interpret or apply it to any individual or specific fact pattern.