Through experiments, we idealize a plant leaf as a flexible, thin, rectangular plate clamped at the midpoint and positioned perpendicular to an airflow. Flexibility of the structure is considered as an advantage at moderate flow speed because it allows drag reduction by elastic reconfiguration, but it can also be at the origin of several flow-induced vibration phenomena at higher flow speeds. A wind tunnel campaign is conducted to identify the limitation to elastic reconfiguration that dynamic instability imposes. Here, we show by increasing the flow speed that the flexibility permits a considerable drag reduction by reconfiguration, compared to the rigid case. However, beyond the stability limit, vibrations occur and limit the reconfiguration. This limit is represented by two dimensionless numbers: the mass number and the Cauchy number. Our results reveal the existence of a critical Cauchy number below which static reconfiguration with drag reduction is possible and above which a dynamic instability with important fluctuating loads is present. The critical dimensionless velocity is dependent on the mass number. Flexibility is related to the critical reduced velocity and allows defining an optimal flexibility for the structure that leads to a drag reduction by reconfiguration while avoiding dynamic instability. Furthermore, experiments show that our flexible structure can exhibit two vibration modes: symmetric and anti-symmetric, depending on its mass number. Because the system we consider is bluff yet aligned with the flow, it is unclear whether the vibrations are due to a flutter instability or vortex-induced vibration or a combination of both phenomena.