New priorities in the heritage conservation field that argue for widespread rehabilitation and maintenance of existing buildings are hampered in Canadian jurisdictions by difficulties contracting appropriately skilled workers to carry out that maintenance. This phenomenon is general, but it is produced by local market conditions and demands locally directed study. In Toronto, the regulatory organization of the heritage sector creates an environment where heritage professionals can flourish while trades skills associated with maintenance decline. This study considers this policy framework in terms of its capacity to support viable careers for heritage tradespeople. Looking at new theories in heritage conservation, emerging concerns in the Canadian heritage conservation sector, and Toronto's culture industries outside of architecture conservation, it argues for a re-evaluation of Toronto's heritage policy to support a robust skilled workforce and ensure that the city can continue to sustainably rehabilitate and maintain its existing building stock.