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Many jobs in Illinois 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 Springfield Tree Service 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.
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.
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 Tree Service 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 Springfield contractors to get to job sites if they lack appropriate vehicles.