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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 Roofing 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 Colonial Heights contractors to get to job sites if they lack appropriate vehicles.
Many jobs in Virginia 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 Colonial Heights Roofing 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 Colonial Heights Roofing 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.
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 Colonial Heights as well, which will give you a broader view of customer satisfaction for a given company.