Web 2.0 is a buzzword introduced in 2003–04 which is commonly used to encompass various novel phenomena on the World Wide Web. Although largely a marketing term, some of the key attributes associated with Web 2.0 include the growth of social networks, bi–directional communication, various ‘glue’ technologies, and significant diversity in content types. We are not aware of a technical comparison between Web 1.0 and 2.0. While most of Web 2.0 runs on the same substrate as 1.0, there are some key differences. We capture those differences and their implications for technical work in this paper. Our goal is to identify the primary differences leading to the properties of interest in 2.0 to be characterized. We identify novel challenges due to the different structures of Web 2.0 sites, richer methods of user interaction, new technologies, and fundamentally different philosophy. Although a significant amount of past work can be reapplied, some critical thinking is needed for the networking community to analyze the challenges of this new and rapidly evolving environment.