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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.
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 Siding 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 Southfield contractors to get to job sites if they lack appropriate vehicles.
The question is great for some industries and non-applicable for others. A general contractor, for example, will by definition employ subcontractors. Most Southfield Siding 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.
These first two questions should only relate to services or good purchased directly from the service provider. Many products carry their own warranties, like roofing shingles or siding. It's useful to know what these warranties cover as well as how long they last. The "warranty agent" question is important, because often warranty agents work with the manufacturer to get you repairs under warranty at a much lower price.