@quietbun, this was at Market St.?
Try riding a normal skateboard on those streets. I grew up skating and it is funny when people complain about 83mm wheels being too small when I rock 53mm wheels with a 100a hardness on those same streets. You will also have more of a problem when you have a board with no tail. If you have a tail you can pop your nose over the pebbles and such which lets you avoid the big stuff. When you skate you learn to pop the nose and float your back foot so you can float over the rocks, it is a skill that takes time to master.
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A weight sensor might be a better solution.
Damn dude. I am starting to concider mechanical brakes that mbs sells with their boards 
If anything goes wrong - i can wiggle my foot - disconnecting the loop key and pulling on the mbs brake. The best and the most reliable controller (again imo) is GT2B or similar. Never failed on me and i never had signal problems. I even modded one into a custom 3D controller and it works wonders.