E-scooters have rapidly become a popular option for first- and last-mile mobility, yet their integration into urban transportation systems has raised significant safety concerns. This study investigates the feasibility of permitting E-scooter riding on sidewalks under controlled conditions to minimize pedestrian conflicts. Analysis of E-scooter crashes in Daejeon, South Korea, showed that 98.09% of crashes were caused by rider negligence, with “Failure to Fulfill Safe Driving Duty” as the leading factor. To investigate the applicability of safe sidewalk usage, a VR-based simulator experiment was conducted with 41 participants across four scenarios with varying sidewalk widths and pedestrian densities, under speed limits of 10, 15, and 20 km/h. Riding behaviors—including speed stability, braking, steering, and conflict frequency—and gaze behaviors were measured. Results showed that riding at 10 km/h improved riding stability and minimized conflicts. Regression analysis identified pedestrian density as the strongest predictor of conflicts, followed by sidewalk width and riding speed. These findings suggest specific policy needs: ensuring a minimum sidewalk width of 4 m for safe shared use, restricting operation to environments with low-to-moderate pedestrian density, and implementing a 10 km/h speed limit. This study provides evidence-based recommendations for safer integration of E-scooters into pedestrian environments.