This purpose of this essay is to start a conversation about expanding the focus in education finance to more comprehensively include the problems of educational inheritance and generational tradeoffs as central to education for generational succession. It is based on both long-term personal experience both as a professor, and as school board member and president. Because of my interpretations of this experience, much of the usual citation list is not included. It is deliberately written in the form of a provocative essay, because its emphasis is less about a search for causal prediction and explanation, and more about engagement in policy framing. This essay has not been created to demonstrate the one best way to succeed. It doesn't even assume some level of certainty is possible. It assumes instead, multiple layers of valid and contradictory meanings. It asks how we should consider looming challenges with both high levels of uncertainty and limited historical precedent. This essay hopes to give these problems greater traction.