Actually, Heller illustrates how difficult it would be for anyone to have challenged any of these laws. For 25 years isn't it, that that handgun ban has been passed, in D.C. The problem with such laws is how do you change them? Heller had it easy, since he was the poster boy for what was wrong. Cop who can't carry a gun in his house? Can't get a license?
Why? P.C. police chief that, like our area, view it as not PC to issue a CCW, so, they don't. How do you challenge that? They actually have a conspiracy by police chiefs that came out in documents to not issue CCW's. What do they do? They only issue to their friends, funding folks, none to the public. That way discrimination suits are difficult, since you don't know why the person got theirs.
Heller was perfect, in that he had no down side, no loss if he wasn't issued the permit. In other words his life didn't come to a screaching halt if the courts had found in favor o f the city regulations. Also, the SC did NOT have to rule on the individual right of the second amendment. They could have made some other stuff up to justify ruling in favor of the city.
Without the Heller case, gun laws are VERY difficult to attack. The only way to really do it is do something illegal, get caught at it, and take it up on appeal. It's called having standing, and, it's usually confined to Constitutional issues, such as a right in the Bill of Rights,
conflict of laws, different rulings on the same issue, by different appellate Federal courts, or, a conflict of laws, on the same issue, state and federal, better known as a Supremacy Clause issue. On top of those limitations, you have to have standing in the issue. Something material that affects your rights, or directly affects you. Without Heller, getting over the standing issue was very difficult.
For 200 years the court has dodged the conflict of law issues with state and federal gun laws. How? By not taking the cases. So, you've had two bodies of law, both pretty much contrary to the 2A, yet, no way to challenge.
By the way, the Big Boy Rule would have put a bunch of guys in jail, otherwise known as the Founding Fathers.
Seems they didn't respect, or follow, a number of laws in effect at the time...