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Amid an acknowledged “affordable housing crisis”, a first-time developer approaches the City to release part of a tax-acquired property, promising a smart-growth development that would provide sorely needed starter homes for working families. The case highlights the complications of balancing competing interests in Portland ME. It shows where rational planning fails in the presence of strong neighborhood opposition, a disjointed city staff structure, and the absence of political will among City Councilors. It highlights the need for champions within local government when a project evokes competing interests. It demonstrates the extent to which “words matter” to policy outcomes, and who gets to define them – in this case, in the fateful difference between “preservation” and “conservation.” Finally, it suggests that NIMBY responses to development proposals may depend as much upon how and by whom it is put forward as by what.