This study evaluates the efficacy of government-incentivized residential building retrofit programs across ten diverse Canadian cities from economic and environmental perspectives. We modeled retrofit strategies using the Vertical City Weather Generator (VCWG v1.4.9) software. We assessed their financial and environmental viability under various jurisdictions with different economic incentive programs and future energy price inflation rates for electricity and fossil fuels. Our findings reveal city-specific variability in retrofit effectiveness, emphasizing the need for tailored approaches. Increasing electricity rates enhances Photovoltaic (PV) systems benefits but diminishes Heat Pump (HP) financial returns. Higher energy costs make retrofits more financially viable and shorten investment payback periods. While most strategies reduce Greenhouse Gas (GHG) emissions, PV systems are particularly environmentally effective when the electricity grid GHG emissions intensities are high. Building Envelop (BE) upgrades benefit all cities with a short payback period. Despite the economic incentives, HP may offer limited financial or environmental benefits. This study underscores the nuanced considerations necessary for effective retrofit policy formulation adapted to local contexts.