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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.
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 Longwood as well, which will give you a broader view of customer satisfaction for a given company.
You'll always want to ask how long the company has been in business in Longwood. 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.
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 Longwood contractor will know how much they need for a deposit when they've given you the estimate, so ask early.