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|Business Categories||Painting in Honolulu, HI|
You'll certainly want to ask them this. Steer clear of any company that is not insured in Hawaii, because that means that any incidental damage they may do on your property will be a real hassle to recover compensation for. It is never wise to work with uninsured tradesmen of any kind. Most states also require that someone have insurance in order to be issued a trade license. If they say they're licensed but not insured, they're being less than truthful.
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.
You'll always want to ask how long the company has been in business in Honolulu. While this isn't a guarantee that the company will do good work, companies with longevity on their side must be doing something right. That being said, there are newer companies that do great work. If the company is under three years old, ask where the owner was employed before and for how long. If he/she has a long history of employment, it's reasonable to infer that he or she decided to go into business for themselves after so many years of experience.
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 Honolulu contractors to get to job sites if they lack appropriate vehicles.