Sling configurations significantly influence the coupled dynamics of the helicopter with slung load system (HSLS), resulting in alterations to handling qualities (HQs) that remain inadequately understood. This study introduces a computer-oriented, generalized method for constructing the HSLS model with various sling configurations. To evaluate the HQs of 1-point, 2-point, and 4-point sling configurations, both the stability and response criteria outlined in ADS-33E and a newly proposed criterion for slung loads towards the updated ADS-33F were employed. Modal analysis was conducted to elucidate the coupled mechanisms of the HSLS under different sling configurations. The findings reveal that the dynamics of the main rotor can attenuate the lateral swing motions of the load in the 4-point sling configuration. While multiple-point sling configurations can enhance the helicopter’s bandwidth, they also amplify the magnitude notch in the helicopter’s response. Nevertheless, when a larger hook distance is employed, the notch frequency is sufficiently distant from the load swing bandwidth, leading to a reduced degradation in HQs. A 4-point configuration with lateral and longitudinal hook distances equal to twice the width and length of the slung load is recommended in practice to achieve sufficient swing stability and mitigate HQ degradation.