How important is it to work with an agent who knows the areas where I am looking?

Extremely important. You don’t want to find out later that about any surprises or overpay for a property. A local expert who has worked the market for years will know the “ins and outs” of a neighborhood- the schools, pricing trends, historical appreciation rates, and they will know whether or not a specific property is realistically priced or may present resale problems down the road.