To evaluate the generalities of acceptability of a proactive braking intervention system, which anticipates an imaginary pedestrian rushing out from occluded areas, and driving environmental dependencies, we conducted field operation tests (FOTs), where 146 elderly drivers participated at three evaluation sites with different urban characteristics. Analyses regarding the coexisting traffic participants illustrate driving environmental characteristics at each evaluation site. Evaluations via TMT-J, DSQ, and WSQ compare the characteristics of experimental participants. Based on these results as premises, we analyze questionnaire answers regarding the proposed system. As a result, we confirm the generalities that more than half of the participants at each evaluation site expressed a desire to introduce the proposed system into their own vehicle.