In the bigger picture, it would be best to get a series of decisions limiting the ability of sate and local governments to do total bans. As noted, NY and Chicago are reasonably easy targets. I would expect the initial case to fail on the local level, and perhaps through the lower appellate courts, with the final victory coming at the SCOTUS level. Once the lower appellate courts have seen their decisions overturned, they will then fall in line.
Once the lower appellate courts have come to understand that there is a right to arms, the time will have come to attack the full auto ban contained in Section 922(o). Sam Adams is right in his statement that this is virtually identical to the DC ban. As he noted the second amendment is directly applicable, this is a federal law, and so there are no states rights issues to address. There are also discrimination issues in the current machine gun laws, for all practical purposes, only the rich are allowed to own these guns. This set of laws should be attacked from that perspective first, and then have the second amendment argument addressed. In the oral arguments for the Heller case, there was a tacit agrement that machine guns fulfill the military portion of the second amendment.
By the way, I really like everallm’s comment:
"Remember children, once we have pulled the pin from Mr. Grenade, Mr. Grenade is no longer our friend." How many times do we forget this important lesson?