You should probably chat with Sai, of Make Your Laws. (http://s.ai/) He's spent a bunch of time recently petitioning the FEC to answer questions about various crazy ways his organization would like to funnel donations. (Specific technical questions, like: "If someone gives us a donation whose recipient is conditional on a condition that won't be known until 6 months from now, [question about how some regulation applies].") I bet he can at least help you find answers.