I think one of the biggest hurdles to less stringent gun laws is the general public perception of gun owners. A lot of people seem to be afraid of gun owners, and think they're all rednecks with trigger fingers (I have many friends and family like this, and I'm sure most of you do too). Hell, I live in a condo building, and after getting constant judgmental stares whenever I walked to and from my car with a rifle bag, I finally stopped going to the range as often.
The funny thing is though that everyone I've met through this site or on the range has been really laid back and chill. Unless and until we can get the popular support, there's no real hope of getting better laws passed.
On a related note, what's to stop someone from opening his own security guard firm, and to constantly be on the job protecting him or herself, or family and friends for that matter?