I am a bit confused as to what you feel this family has done that needs to be "reported up the chain of command" (not to mention who that "higher up" would be).
I am also a bit confused as to why you are dealing with the mother, and not the Boy Scout.
I get it that the mother is a bit hard to deal with, and does not respond to questions. However, while that can be a pain in the rear, it is hardly cause for "reporting" her.
What "conventions and practices" have they not followed?
What is so bad about selling "solo"? Why must all selling be done with other Troop members?
Even at the Cub level we encourage the boys to sell to their neighbors, and for their parents to take a sheet to their workplace. Why would Boy Scouts not be allowed to do this?
Let's face it, if a boy is going to sell $5,000+ worth of popcorn, he is not going to do it selling only at Troop booth sales.
For the multiple sheets of military donations, personally I think that is great, and what I would encourage my family and friends to do. You help Scouts, you help the military, and you don't have to eat popcorn you don't really want. There is no need to sign your name to the sheet as there is nothing to be delivered.
I do not understand why you say this Boy Scout has not "earned" his top seller status. You were not there with him, and do not know how much of a contribution he made to the sales. Even if you are correct, and his parents were the only ones to actually purchase any popcorn from him, he still "sold" it.
As to the shoebox with 5,000+ dollar bills in it, yes, that would tic me off a bit. However, have you considered that they might have done that as a kind of payback for how you treated them during the sale? No, that does not make it OK, but at least it makes it understandable.
For popcorn sales my main sticking points are -
1) Are the Take-Order forms turned in on time?
2) Is the product picked up in a timely fashion?
3) Is all money due turned in on time?
If I do not have to try to add last minute orders after the drop dead date, threaten with collection to get money, or eat a loss, I am a happy Popcorn Kernel.
Not having to call, and chase, to reach that goal would be extremely nice too, but I am realistic, and do not expect miracles!