What is the Catholic teaching on selling things on the black-market, or without the full sanction of the law?

If you buy or sell something on the black market, or without the permit or license required by law, how much culpability is there?

And if you made some money doing it, would your children have to make restitution in order to inherit heirlooms, memorabilia (etc.) from you after your death?

I think this is a very important question, especially as the government gets more and more unjust and invasive of personal rights (For example, forbidding the sale of raw milk, requiring that all gold sales over $600 be reported, or forbidding second-hand dealers from accepting or paying cash in the state of Louisiana)

But it's not just unjust laws -- there are just laws as well. For example, certain goods require a license to sell them (alcohol, tobacco, prescription drugs). What if you create your own alcohol and sell it, import cigarettes from Mexico and re-sell them without charging/paying the federal tax, or sell unused prescription drugs to friends/family?

Most commerce laws on the books have no basis in morality and are either in place for the purpose of generating revenue or for protecting a class of people who have political influence.  While one may be prosecuted for disobeying them, I do not believe any actual sin is committed.

Selling something that is misrepresented (e.g., a Chinese-made imitation of a Rolex watch that is intentionally marked as if it is truly a Rolex) is both illegal and immoral.  On the other hand, performing a service that need no formal education (e.g., cutting hair, styling hair, taxi services, etc.) that require a license only because the State wants a cut and those already in the occupation have the political influence to limit competition is not immoral (in my opinion) though I think one would be morally obligated to pay taxes as required by law (that is, render to Caesar...).

All of the examples given, may not be morally sinful in themselves, though escaping or evading law enforcement may lead to other sinful actions and the temporal consequences of detection by law enforcement may make it unwise to engage in those activites.

Ticket scalping, by the way, of authentic tickets is simply a free exchange of goods.  The investors who buy tickets in the hopes of selling them at a higher price are taking an economic risk and if they find customers who are willing to pay their price, they make a free and fair trade.  It is not against the law because anything immoral is done, but for other reasons.  In order to be eligible to host the Superbowl in Indianapolis this year, the city had to pass an ordinance making scalping illegal within a certain distance from the stadium, so they passed a temporary ordinance,  otherwise scalping is legal in Indianapolis as long as it is not on Lucas Oil Stadium property.  This law was passed merely to let the NFL present a certain appearance.  (What I never understood were the scalpers at Mariners games during the 1970s when the team was always in last place and there were always plenty of good seats available.  Why on earth would people buy tickets from scalpers at a higher price?  Those guys must have lost a fortune!)