Conservation of cultural built heritage in society has become vexed with political, financial and planning difficulties. The listed stock is in gross need of information, funding and policy direction. Opportunities to capture value, to maximise conservation incentives and generally to encourage owners to maintain their listed heritage properties, are being sorely missed. Yet, the survival of the heritage listed stock is dependent upon flexibility, consistency and certainty in the system. To what extent do current controls cope with adaptive re-use, continually evolving aspects of cultural significance and a need to keep the purpose of heritage listing alive and relevant? Attitudes and opinions of heritage practitioners, owners, developers, managers, planners, lawyers and policy makers working within the NSW heritage sector, have been documented in recent PhD research undertaken by the author at the Faculty of the Built Environment - University of NSW. The area of the study is confined to the NSW heritage management system at local government level. The paper records the attitudes and opinions of at least 50 separate interviewees and provides leading evidence of systemic failure in current local government planning frameworks. The paper attempts to analyse internal and external pressures upon such frameworks and alludes to future policy development in the sector by way of incentives, funding schemes and innovation.