stove doesn't really have any reason to apologize. he was right. haul your arse out to the woods and try it. i haven't the foggiest as to whether you've 'legally' camped before, but if you have, and you're on any decent-sized patch of land, you'll know that the ratio of rangers/DNR personnel to square miles of land is awfully low.
ergo, unless you're being a dipshit (ex: camping within sight or ear shot of a trail, making poor fires that belch more smoke than heat, etc, etc) or you're especially unlucky, or you're setting up permanent residence, you don't have too much to worry about.
and what's annoy about your questions is that you come across as being whiny, needy, and having no original thoughts whatsoever. i get what you're asking for, but christ:
"Also, how hard of a time do you have getting back to town/city to re-up on resources? Do you leave your camp up, or pack it every time? Ever worried about your gear getting jacked? Do you stash it?"
what the hell kind of question is that? do you want me to look into my crystal ball, predict where it is you'll be camping, and give you the answer??? like just about everything in life, the answers, insofar as they exist, lie in the particulars. in other words: the solutions that work well for one given set of conditions and locations will probably not work well in another. so don't go looking for specific 'please mommy, hold my hand' answers to very vague questions.