The biggest obstacles in my opinion are fear and ignorance. We can allay fear only by being an examples of a firearms owners who brings safety, security, and our basic humanity along with our vehement defense of our rights. Nothing is more threatening to a person unfamiliar with firearms than an angry gun owner.
Ignorance is more difficult to combat because media reinforces it everyday. Shooting sports are a great vehicle for increasing familiarity and combating ignorance, because we live in a world where everyone expects to entertained, and everything's a contest these days: Iron Chef, America's got talent, etc.
If you can make a fierce competition out of cooking dinner, surely an IPSC match could be filmed to be compelling television. On the side, It could feature the competitors being interviewed talking about how important the right is to preserving our liberty, dignity, and way of life. They could discuss gun safety and teach the public important gun handling lessons.