I partly disagree that a comfortable monthly cost is enough. Retail property can have thin transaction volume, so the apparent market price may be based on a small and uneven sample. If nearby evidence consists mainly of asking prices, a buyer could be financially comfortable and still overpay...
The insurance concern should be investigated independently of the physical inspection. A building can appear sound while a coverage limitation, exclusion or high excess changes your exposure. Ask what is actually insurable and on what terms before deciding that inspection findings are the only risk.