Strong winds or typhoon disasters pose significant risks to historical buildings in many countries and regions. Although numerous researchers have discussed the damage caused by natural wind disasters, little attention has been paid to the potential impact of renovation and adaptive reuse strategies on the wind resistance performance of historical buildings—an avoidable human-induced factor. This study selected the representative ancestral hall building in Guangzhou, namely Lujiang Academy, for on-site investigation and Computational Fluid Dynamics (CFD) simulation analysis. It examined two renovation approaches: installing glass curtain walls around the courtyard and enclosing the top of the courtyard with a glass canopy. This study also assessed the roof wind pressure distribution in its unaltered state to evaluate the impact of different renovation strategies on roof wind load distribution. The results showed that installing glass curtain walls can effectively reduce the upward suction effect on the main hall roof, thereby improving its wind resistance performance. Conversely, enclosing the courtyard with a glass canopy may increase negative pressure on areas such as the eaves and corridor roofs, raising the risk of roof damage. This study systematically evaluated the renovation strategies for historical buildings, detailing the specific impacts of different retrofit measures on the wind resistance performance of building roofs. The methods and findings are significant not only for the renovation of ancestral hall heritage buildings in Guangzhou but also for providing practical scientific methods and technical strategies for the conservation and renovation of similar historical structures. This research demonstrates an effective approach to enhancing wind resistance and preventive protection for historical buildings.