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This will be answered when you ask if all employees are licensed. The only way to obtain a legitimate tradesman's license is to be a legal or naturalized citizen of the US. The company may employ people in positions that don't require a license, however, so it's wise to inquire.
Always ask for references, and always check them. Keep in mind though that the only references you'll get are people who the contractor is certain will give him a good review. You'd also be well advised to check online review sources in Wrentham as well, which will give you a broader view of customer satisfaction for a given company.
Many jobs in Massachusetts will require municipal permits in order to be approved by the town's inspector. It's always good to ask who will be responsible for pulling those permits, and if you'll be expected to do it. You'll almost never be told to pull your own, but knowing that Wrentham Painting permits are required makes you appear to be a well informed customer.
This really only matters if you have a preference, but it is good to ask. If you have a strong ideological belief about unions or nonunions, it's perfectly acceptable to make a decision based on the preference.
The question is great for some industries and non-applicable for others. A general contractor, for example, will by definition employ subcontractors. Most Wrentham Painting companies do not, but there are exceptions. You should always ask this question to your service providers. If they do use subcontractors, ask if they're all licensed and insured independently.