Way too many things to go wrong and it's not like you can eddy out when it does. I've jumped out of lots of airplanes and I'm not sure I'd do it with a kayak. Bad for folks on the ground if you have to lose the kayak and I think the FAA still frowns on dropping stuff on people from 10,000 feet.
On the other hand this is probably all a Riot kayak is good for. 
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At least once every human should have to run for his life, to teach him that milk does not come from supermarkets, that safety does not come from policemen, that news is not something that happens to other people. ~ Robert Heinlein
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