I had these exact same questions: riding in Seattle/SF and Cleveland. I don't think there's any way to make a safe powerful brake system for skateboards unless

I had these exact same questions: riding in Seattle/SF and Cleveland. I don't think there's any way to make a safe powerful brake system for skateboards unless you're ready to do the stale fish maneuver, i.e. hit the brake button and grab the board, which, if there's a kiteboard-style handle, seems plausible OTW, you have to learn power slides to make drastic decelerations, or bail off the front and kick the board behind you, but I almost got run over a few times in SF doing that. This also only works if you're not going faster than you can run. I found that out empirically too Not really relevant, but i saw somebody a couple years ago ride a shopping cart full of bottles (probably weighed a couple hundred pounds) down the steep hill on Haight st from Baker to Divis. He's my hero