I was able to get this in one shot. There are a never ending supply of Flipper looters in the spot below, which is 5-1 Eldertown. Once you spawn some looters here, press
with the Omni Boots equipped. Keep yourself between the chariot and the looters and they will try to flip you several times. Bang the chariot on the ground to spawn more in the same spot, and use the boots again. Once the 10th flip hits you but doesn't affect you, you'll earn this achievement.