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Hi - my name is XXXXX XXXXX I'm a litigation attorney. Thanks for your question.
You are correct that tobacco is a highly regulated commodity, and in order for your husband to be able to legally sell tobacco products, he would need a sales permit from the local city/county authorities.
Also, he would have to apply for a license through the Mass. Dept of Revenue. There are multiple licenses that are out there, which you can find here: http://www.mass.gov/dor/forms/cigarette-and-tobacco/
Thus, to be 100% legal, he would have to go through all of these hoops. It is a hassle, but if he were to get caught selling these items, he would likely be fined and penalized for failing to obtain a license.