In this 'Thinking Space' essay we revisit Maurie Daly's 1982 book Sydney Boom, Sydney Bust, fuelled by concern for how Australian cities are being transformed by financialised real estate. Daly's insights remain highly relevant to Sydney and other cities around Australia and the world today. Poorly planned densification, inflated property markets, land speculation, and housing poverty are all outcomes of the (global) capitalist intersection of finance and land in Australia. The overwriting of Aboriginal country with colonial-capitalist systems of land ownership set in train a process of land and housing booms, bubbles and busts that are better understood by their circular continuity rather than as a set of ephemeral ruptures. It is the property and finance system itself, rather than any ruptures to it, that reproduces unequal and alienating social relations. Researchers investigating property speculation, global capital, urban planning and financialisation, we argue, ought to revisit this key text to inform their contemporary analyses. Moreover, those wielding power over Australian urban affairs would do well to read it too, lest its lessons be ignored for another generation.