This paper outlines some challenges for the Web Observatory vision with reference to field notes from a student exchange and research collaboration in December 2013 between the University of Southampton, Tsinghua University and KAIST. These field notes outline a methodological narrative of the practical challenges that we faced in using the Web Observatory in collaborative research. It is suggested that these challenges particularly come in the form of technical, organizational and legal issues. The paper concludes with some proposals for the future of the Web Observatory vision.