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Many jobs in New York 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 Ridge Painting permits are required makes you appear to be a well informed customer.
The question is great for some industries and non-applicable for others. A general contractor, for example, will by definition employ subcontractors. Most Ridge 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.
This is important mostly for larger jobs. Clearly a two man operation is going to build a home much slower than a 15 man crew. This is also a good indication of the overall size of the Painting company, if that's an area of concern for you. The reason you may want to ask about the fleet is that fleet size is a good indicator of the mobility of the company. Mobility may not sound important, but it's hard for the Ridge contractors to get to job sites if they lack appropriate vehicles.
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.