Wireless mesh networks have the potential to provide ubiquitous high-speed Internet access at low costs. The good news is that initial deployments of WiFi meshes show the feasibility of providing ubiquitous Internet connectivity. However, their performance is far below the necessary and achievable limit. Moreover, users' subscription in the existing meshes is dismal even though the technical challenges to get connectivity are low. This paper provides an overview of the current status of mesh networks' deployment, and highlights the technical, economical, and social challenges that need to be addressed in the next years. As a proof-of-principle study, we discuss the above-mentioned challenges with reference to three real networks: (i) MagNets, an operator-driven planned two-tier mesh network; (ii) Berlin Freifunk network as a pure community-driven single-tier network; (iii) Weimar Freifunk network, also a community-driven but two-tier network.