Ameriscape has 12-13 trucks (I can't remember) and couldn't get us done on time. They would bring 3 trucks to my neighborhood (about half the size of the neighborhood in the OP) and it would take them 2 hours to plow. That was with only making 1 of the contracted 3 passes in each alley way.
You are saying your company with 5 trucks could guarantee that it would be done properly on time, each and every time?
If so, please, call my HOA. They would hire you in a heartbeat.