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Though a standard question, it's important to ask. Most contractors will tell you how long they expect the job to take without you asking. If they don't volunteer that information, be sure to ask. It's also helpful to ask if that's a hard finish date, meaning that it's the definite finish date. If it's a soft finish date, it may be extended for any number of reasons.
Many jobs in Colorado 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 Littleton Siding permits are required makes you appear to be a well informed customer.
Some companies may require a 10% deposit, some may not require any. For larger projects, you'll almost always need to give a deposit, and it's good to ask how much the deposit will be before going forward with a project. The Littleton contractor will know how much they need for a deposit when they've given you the estimate, so ask early.
You'll always want to ask how long the company has been in business in Littleton. 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.