The purpose of this chapter is to provide guidelines for city governments considering implementing large-scale wireless networks to provide Internet access for their citizens and businesses. Case studies of cities in the United States that have implemented wireless networks will be evaluated in the context of opportunities and potential challenges. Some key considerations discussed in this chapter involve free versus fee-based models, security considerations, conflicts with local telecommunications companies, and network support. Opportunities to benefit police and emergency services are examined in terms of potential benefits as well as considerations of security in mission critical situations. Strategy guidelines will be presented as a means for providing structure to this decision-making process.