Originally Posted by NesquikNinja
... To you more experienced guys, how do you determine what is fair game and what is illegal/disrespectful as far as aleaving the pavement goes?
That probably has more to do with your location than anything else. Where I am, touching the front wheel to dirt that is outside of my yard or not a public road is almost guaranteed to be illegal. Legality and enforceability are quite different though, and often local law enforcement is lenient as long as you're not being a loud, obnoxious, offensive brute. Not that I want to step on a soapbox, but this is how loud exhaust does not help. If you're already breaking the law, a loud exhaust just provides the incentive to call you on it. Not all of us have vast expanses of legal off-road riding areas where noise might be less of a concern.
Otherwise, if it looks like someone has gone out of their way to post no-trespassing, that's a sure sign to stay out. If something looks well-traveled, it may be acceptable, or it may be the landowner's own equipment. Get friendly with local landowners to find out. Sometimes utility companies allow riding, such as power lines and gas lines. It can actually help them, as it keeps a passable trail on the line. Otherwise the vegetation may grow in which would then require them to cut it back to keep access available for them. Again, quiet and polite go a long way. If you dig a trench holding it WFO with the front brake on, you may not be allowed back there again. Give a friendly wave to anyone you see. Anything you do to show you're an upstanding, contributing member to society helps. Even the visual difference between a well-maintained bike and one falling apart can present a different image of who you are. We're only allowed to ride while the public non-riding majority allows us to.
In the last 20 years, places that are acceptable to ride have shrunk by vast amounts (at least near where I am). People appear to be much more "protective" of their land than they used to be. Likely in part at least due to legal responsibility issues. All that said, a CRF250L or similar small dual-sport is probably a very good choice as not only is it non-intimidating to ride, but it's non-intimidating to potential on-lookers, who may have the power to make your life miserable.