Two connection types are examined under a life-cycle point of view, for a regular framed steel hotel building located in Mexico under a strong wind hazard, to compare their cost-effectiveness and provide practical recommendations. Although FEMA has fragility curves for housing facilities under strong winds, there are no curves for medium height or tall buildings like the one used to illustrate the formulation. The critical connections were identified through a series of preliminary analyses of the ten stories building, which were performed under scenario wind velocities, and a detailed finite-element model was used to evaluate the connection limit state and the failure probability at both levels: the connection and the overall building. The cost-effectiveness of bolted and welded connections was examined, as alternative designs, through the calculation of the expected life-cycle cost. Envelope damages are explicitly considered as facade components and windows are usually damaged and cause important losses. In addition, the potential loss of contents is assessed as a consequence of water infiltration after the building envelope is damaged, and the expected business interruption losses, from the repairs required, are included in the cost analysis. The correlation coefficient between wind velocity and rainfall intensity, given the occurrence of a hurricane, is calculated and incorporated on the simulation of rainfall intensity. Recommendations to mitigate losses are proposed in terms of the fragilities found and the cost of mitigation measures. It is shown that low-cost improvements, on the facade and windows anchorage conditions, strongly reduce the expected losses and the cost–benefit of these measures decreases as the building importance increases.