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Just a follow on thought Hippiedude.... If you are going to put something in the stake holes to help hold them in place just a little design suggestion .. Make them smaller at the top on all four sides and taper to almost the right width where the trailers will meet. This will make it easier...

Just a thought.. I am not too smart and do not know those trailers very well but..... If you know going in that you are going to stack them like that can u put something (2X4) in the rail holders? This would prevent them from sliding off and add a measure of safety.