Since 2017, Taipei City government has implemented a policy to expand the rental housing market with a set of incentives for landlords that brings more affordable apartments to the market. This study applied visual content analysis to online rental housing advertisements to investigate the private rental market’s ability to provide adequate housing. The results show limited supply in the affordable price range, structural deficits, and elements contributing to an unsafe and unhealthy living environment. Also, accessibility is not ensured, as 91% of the units are in walk-up buildings. In addition, the prospects of the current policy direction for improving tenants’ precarity in the private rental market are weak, as discrimination and lease insecurity are not being addressed. This paper discusses the potential adverse effects of the current policy direction, including hindering urban regeneration efforts and fuelling a ‘Generation Landlord’. A tenant-centred, multidimensional approach to affordability is recommended as a starting point for future policy design.