My philosophy is to do EVERYTHING that you are allowed to do. That means if there is a definite border of what's ok under the rules in any given place, when you are in that place you should do everything UP TO what's allowed there, but make sure you don't cross the line and violate the rules. Sometimes you'll accidentally cross the line and get in trouble, but that just helps you better know exactly where the line is drawn. Then next time you'll be able to approach the "good versus bad" boarder closely without actually crossing it.
Why push the rules? How about because if you don't use it you lose it. If you don't take full advantage of the range of what's allowed, people in charge will think they can get away with tightening the restrictions, and begin to deny freedoms. If you show those in charge that the full extent of what's allowed is indeed being taken advantage of, those in charge will realize that they can NOT tighten the rules without encroaching on freedom, and that will force them to not tighten the rules, and perhaps they will even loosen them.
I say that when one has the freedom to do certain things, that you should do every one of those things which you are allowed, else those in charge might start telling you that you can do fewer and fewer things with each new rule they make.