This paper explores the question “What is the appropriate level of investigation when conducting a structural building condition review?” Certainly, the premise of the review is a factor - be it to assess the building prior to its purchase, to consider its repurposing or rehabilitation, or to address a concern about a symptom, such as wall cracks or other apparent structural distress. But in most cases an overarching purpose is to increase the level of confidence in a building’s future ability to structurally perform its intended function. What is our obligation to our clients to accomplish this end? The protocol for a condition review of a structure is frequently limited to a set of observations to determine if there is any visually apparent evidence of distress, damage, or deterioration. Yet some structures have hidden defects, created either in design or construction, that represent capacity limitations that analysis would show could be conditions of high overstress under service loads. Such hidden structural limitations have led to sudden collapses. When should further analysis be considered when conducting a condition review? The author proposes a decision matrix which takes into account more than visually apparent signs of structural deficiency in an existing building, in order to more reliably develop an opinion of future performance.