The question is too open ended. What are the problems facing the city? Is it growing or shrinking? Does it have budget issues or is it well managed? How is

The question is too open ended. What are the problems facing the city? Is it growing or shrinking? Does it have budget issues or is it well managed? How is it weathering the recession? I suppose this partly answers your question about what to ask on the first day - it should be clear to most people in government in that town what the pressing concerns are - then you can move to solutions.