The trends over the recent years show an increase in streaming media transported across the Internet in addition to al- ready abundant web traffic, increasing the need for distri- bution schemes that efficiently handle this type of traffic. There are two obvious bottlenecks in any content distribution system, namely the origin server and the network. Our goal is to address both these bottlenecks simultaneously by using cooperative caching proxies on top of an overlay net- work. State of the art solutions within both subsystems utilize self-organization. Just combining these two can enable them to work together but may lead to a reconfiguration loop problem. In this report, we identify the challenges of combining these two subsystems, give an intuitive example illustrating the problem, and proceed to give an outline for several different solutions.